Substituted diphenylamine compounds, preparation method and use thereof

ABSTRACT

Substituted diphenylamine compounds of general formula I are provided, in which each substituted group is defined as in the description. The compounds of general formula I have broad-spectrum fungicidal activity in the field of agriculture. Furthermore, the preparation methods of the above compounds are simple.

FIELD OF THE INVENTION

The invention relates to fungicide in agricultural fields, specifically to a kind of substituted diphenylamine compounds and the preparation methods and use thereof.

BACKGROUND OF THE INVENTION

Diphenylamine and fluazinam are known fungicides, the former is mainly used to control storage diseases of fruits and vegetables, and the latter is mainly used to control diseases of field crops.

The compounds having the following general formulas were reported as insecticides, acaricides, fungicides, herbicides, rodenticides or others in the prior art:

Such as patents BR7900462, CH626323, CN1188757, DE2509416, DE2642147, DE2642148, EP26743, EP60951, GB1544078, GB1525884, JP58113151, JP64001774, JP01186849, WO2002060878, WO2005035498, WO2009037707, U.S. Pat. No. 3,948,957, U.S. Pat. No. 3,948,990, U.S. Pat. No. 4,041,172, U.S. Pat. No. 4,152,460, U.S. Pat. No. 4,187,318, U.S. Pat. No. 4,215,145, U.S. Pat. No. 4,304,791, U.S. Pat. No. 4,316,988, U.S. Pat. No. 4,407,820, U.S. Pat. No. 4,459,304, U.S. Pat. No. 4,670,596 and so on, and ACS Symposium Series (1992), 504 (Synth. Chem. Agrochem. III), 336-48; Journal of the Chemical Society (1951), 110-15, etc. all reported the compounds having above general formulas.

In addition, the compounds of the following general formulas were mentioned in Chemische Berichte (1962), 95 1711-21; Chemische Berichte (1963), 96(7), 1936-44; Journal of Organic Chemistry (1954), 19, 1641-5; Journal of the Chemical Society; Transactions (1913), 103 982-8 and Journal of the Chemical Society, Transactions (1921), 119, 187-92 and so on, but without any bioactivity reported.

The preparation method of the following compound was published in U.S. Pat. No. 3,107,263:

The compounds having the structure of general formula I were not reported in the prior art.

SUMMARY OF THE INVENTION

New pesticides with novel structure and excellent property are needed by modern agricultural production. The object of the present invention is to provide a kind of substituted diphenylamine compounds to control a variety of plant pathogens/diseases at very low doses, which can be used to prepare substances to control pathogens in agricultural and other fields.

Detailed descriptions of the invention are as follows:

The present invention provides a kind of substituted diphenylamine compounds having general formula I:

Wherein:

R₁ is selected from H, C₁-C₁₂alkyl, C₃-C₁₂cycloalkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₁-C₁₂alkoxylC₁-C₁₂alkyl, C₁-C₁₂alkoxyC₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylaminothio, C₂-C₁₂ dialkylaminothio or CO—X—CO₂R₉, in which X is selected from (CHR₉)n, CR₉═CR₁₀ or C₆H₄, n=1-6;

R₂ is selected from halogen, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₃-C₁₂cycloalkyl, C₂-C₁₂dialkylamino, C₃-C₁₂alkenyloxy, C₃-C₁₂haloalkenyloxy, C₃-C₁₂alkynyloxy, C₃-C₁₂haloalkynyloxy, C₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkylcarbonylamino, C₁-C₁₂alkylsulfonyloxy, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkoxy, or the following groups unsubstituted or substituted with 1-5 R₁₁: aryloxy, arylamino, arylmethoxy, arylmethyl amino, heteroaryloxy or heteroarylamino, and when the number of the substitutes is more than 1, R₁₁ may be the same or different;

R₃ is selected from H, halogen, NO₂, CN, C(═O)NR₉R₁₀, C(═S)NR₉R₁₀, C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂haloalkyl or C₁-C₁₂alkylsulfonyl;

R₄ and R₈ may be the same or different, respectively selected from H, halogen, CN, NO₂, OH, CO₂H, C(═O)NR₉R₁₀, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonyloxy, or the following groups unsubstituted or substituted with 1-5 R₁₁: aryl, arylmethyl, aryloxy, arylamino, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, arylaminocarbonyl or heteroaryloxy, and when the number of the substitutes is more than 1, R₁₁ may be the same or different;

R₅ and R₇ may be the same or different, respectively selected from H, halogen, CN, NO₂, OH, CO₂H, C(═O)NR₉R₁₀, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylaminocarbonyloxy, C₁-C₁₂alkylsulfonyloxy, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂haloalkoxyC₁-C₁₂haloalkoxy, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkoxy, or the following groups unsubstituted or substituted with 1-5 R₁₁: aryl, arylmethyl, aryloxy, arylamino, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, arylaminocarbonyl or heteroaryloxy, and when the number of the substitutes is more than 1, R₁₁ may be the same or different;

R₆ is selected from H, halogen, CN, NO₂, OH, CO₂H, C(═O)NR₉R₁₀, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂haloalkoxyC₁-C₁₂haloalkoxy, C₁-C₁₂alkylcarbonyloxy, or the following groups unsubstituted or substituted with 1-5 R₁₁: aryl, arylmethyl, aryloxy, arylamino, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, arylaminocarbonyl or heteroaryloxy, and when the number of the substitutes is more than 1, R₁₁ may be the same or different;

But R₄, R₅, R₆, R₇ and R₈ can not be H simultaneously;

R₉ and R₁₀ may be the same or different, respectively selected from H or C₁-C₆alkyl;

R₁₁ is selected from halogen, NO₂, CN, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆alkynyloxy, C₃-C₆haloalkynyloxy, C₁-C₆haloalkylthio, C₁-C₆haloalkylcarbonyl, C₁-C₆alkylamino, C₁-C₆haloalkylamino, C₂-C₈dialkylamino, C₁-C₆alkylcarbonylamino, C₁-C₆haloalkylcarbonylamino, C₁-C₆alkylaminocarbonyl or C₁-C₆haloalkylaminocarbonyl;

Or the salts of the compounds having general formula I.

The preferred compounds of general formula I of this invention are:

R₁ is selected from H, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆ alkoxycarb onyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfonyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkoxyC₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, C₁-C₆alkylaminothio, C₂-C₆ dialkylaminothio or CO—X—CO₂R₉, in which X is selected from (CHR₉)n, CR₉═CR₁₀ or C₆H₄, n=1-3;

R₂ is selected from halogen, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylamino, C₁-C₆haloalkylamino, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfonyl, C₂-C₆dialkylamino, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₃-C₆alkynyloxy, C₁-C₆alkylcarbonyloxy, C₁-C₆alkylcarbonylamino, C₁-C₆alkylsulfonyloxy, C₁-C₆alkoxyC₁-C₆alkoxy, C₁-C₆alkoxycarbonylC₁-C₆alkoxy, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, benzyloxy, benzylamino, pyridyloxy or pyridylamino;

R₃ is selected from Cl, Br, F, NO₂, CN, C(═O)NR₉R₁₀, C(═S)NR₉R₁₀, CO₂CH₃, CF₃ or SO₂CH₃;

R₄ and R₈ may be the same or different, respectively selected from H, halogen, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, or the following groups unsubstituted or substituted with 1-4 R₁₁: phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy;

R₅ and R₇ may be the same or different, respectively selected from H, halogen, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylamino, C₁-C₆haloalkylamino, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl or C₁-C₆alkoxyC₁-C₆alkyl;

R₆ is selected from H, halogen, CN, NO₂, CO₂H, C(═O)NR₉R₁₀, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆haloalkoxy, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, C₁-C₆alkoxyC₁-C₆alkoxy, or the following groups unsubstituted or substituted with 1-4 R₁₁: phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy;

But R₄, R₅, R₆, R₇ and R₈ can not be H simultaneously;

R₉ and R₁₀ may be the same or different, respectively selected from H or C₁-C₃alkyl;

R₁₁ is selected from halogen, NO₂, CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkylamino, C₂-C₆dialkylamino, C₁-C₃alkylcarbonylamino or C₁-C₃alkylam inocarbonyl;

Or the salts of the compounds having general formula I.

Furthermore, the preferred compounds of general formula I of this invention are:

R₁ is selected from H, C₁-C₃alkyl, C₃-C₆cycloalkyl, C₁-C₃alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃haloalkylthio, C₁-C₃alkylsulfonyl, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃alkoxyC₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, C₁-C₃alkylaminothio, C₂-C₆dialkylaminothio or CO—X—CO₂R₉, in which X is selected from (CHR₉)n, CR₉═CR₁₀ or C₆H₄, n=1-3;

R₂ is selected from Cl, Br, F, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, C₁-C₃alkylthio, C₁-C₃haloalkylthio, C₁-C₃alkylsulfonyl, C₂-C₆dialkylamino, C₃-C₄alkenyloxy, C₃-C₄haloalkenyloxy, C₃-C₄alkynyloxy, C₁-C₃alkylcarbonyloxy, C₁-C₃alkylcarbonylamino, C₁-C₃alkylsulfonyloxy, C₁-C₃alkoxyC₁-C₃alkoxy, C₁-C₃alkoxycarbonylC₁-C₃alkoxy, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, benzyloxy, benzylamino, pyridyloxy or pyridylamino;

R₃ is NO₂;

R₄ and R₈ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₂-C₃alkenyl, C₂-C₃alkynyl, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy;

R₅ and R₇ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, C₁-C₃alkylthio, C₁-C₃haloalkylthio, C₂-C₃alkenyl, C₂-C₃alkynyl, C₁-C₃ alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl or C₁-C₃alkoxyC₁-C₃alkyl;

R₆ is selected from H, Cl, Br, F, CN, NO₂, CO₂H, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃haloalkoxy, C₂-C₃alkenyl, C₂-C₃alkynyl, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃ alkoxyC₁-C₆alkyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, C₁-C₃alkoxyC₁-C₃alkoxy, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy;

But R₄, R₅, R₆, R₇ and R₈ can not be H simultaneously;

R₉ and R₁₀ may be the same or different, respectively selected from H or C₁-C₃alkyl;

R₁₁ is selected from Cl, Br, F, NO₂, CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl or C₁-C₃alkylaminocarbonyl;

Or the salts formed from the compounds of general formula I with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methylsulfonic acid, p-toluenesulfonic acid, malic acid or citric acid.

Even more preferred compounds of general formula I of this invention are:

R₁ is selected from H, C₁-C₃alkyl, C₃-C₆cycloalkyl, C₁-C₃alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃haloalkylthio, C₁-C₃alkylsulfonyl, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃alkoxyC₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, C₁-C₃alkylaminothio, C₂-C₆dialkylaminothio, COCH₂CO₂R₉, COCH₂CH₂CO₂R₉, COCHCH₃CO₂R₉, COC₆H₄CO₂R₉ or COCH═CHCO₂R₉;

R₂ is selected from Cl, Br, F, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, C₁-C₃alkylthio, C₁-C₃haloalkylthio, C₁-C₃alkylsulfonyl, C₂-C₆dialkylamino, C₃-C₄alkenyloxy, C₃-C₄haloalkenyloxy, C₃-C₄alkynyloxy, C₁-C₃alkoxyC₁-C₃alkoxy, C₁-C₃alkoxycarbonylC₁-C₃alkoxy, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, benzyloxy, benzylamino, pyridyloxy or pyridylamino;

R₃ is NO₂;

R₄ and R₈ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, phenoxycarbonyl or anilinocarbonyl;

R₅ and R₇ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, C₁-C₃alkylthio, C₁-C₃haloalkylthio, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl or C₁-C₃alkoxyC₁-C₃alkyl;

R₆ is selected from H, Cl, Br, F, CN, NO₂, CO₂H, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃haloalkoxy, C₂-C₃alkenyl, C₂-C₃alkynyl, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxyC₁-C₆alkyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, C₁-C₃alkoxyC₁-C₃alkoxy, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl or anilinocarbonyl;

But R₄, R₅, R₆, R₇ and R₈ can not be H simultaneously;

R₉ and R₁₀ may be the same or different, respectively selected from H, CH₃ or C₂H₅;

R₁₁ is selected from Cl, Br, F, NO₂, CN, CF₃, CH₃, OCH₃, SCH₃, formyl, CO₂CH₃ or CONHCH₃;

Or the salts formed from the compounds of general formula I with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methylsulfonic acid, p-toluenesulfonic acid, malic acid or citric acid.

The most preferred compounds of formula I of this invention are:

R₁ is selected from H, CH₃, C₂H₅, cyclopropyl, formyl, COCH₃, COCF₃, CO₂CH₃, CO₂C₂H₅, SCCl₃, SO₂CH₃, SO₂C₂H₅, CH₂OCH₃, CH₂OC₂H₅, CH₂CH₂OCH₃, COCH₂OCH₃, CH₂COOCH₃, SNHCH₃, SN(CH₃)₂, COCH₂CO₂H, COCH₂CO₂CH₃, COCH₂CH₂CO₂H, COCH₂CH₂CO₂CH₃, COCHCH₃CO₂H, COCHCH₃CO₂CH₃, COC₆H₄CO₂H, COC₆H₄CO₂CH₃, COCH═CHCO₂H or COCH═CHCO₂CH₃;

R₂ is selected from Cl, Br, F, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, SCH₃, SC₂H₅, N(CH₃)₂, N(C₂H₅)₂, OCH₂OCH₃, OPh, NHPh, OCH₂Ph, NHCH₂Ph, 4-chlorophenoxy, 4-chlorophenylamino, 2-chloro-4-(trifluoromethyl)phenoxy, 2-chloro-4-(trifluorom ethyl)phenylamino, 3-chloro-5-(trifluoromethyl)pyridin-2-yloxy or 3-chloro-5-(trifluoromethyl)pyridin-2-ylamino;

R₃ is NO₂;

R₄ and R₈ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NH₂, C(═O)NHCH₃, C(═O)N(CH₃)₂, CH₃, C₂H₅, CF₃, OCH₃, OC₂H₅, OCF₃, SO₂CH₃, SO₂C₂H₅, COCH₃, COC₂H₅, CO₂CH₃, CO₂C₂H₅, OPh, NHPh, CO₂Ph or CONHPh;

R₅ and R₇ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NH₂, CH₃, CF₃, OCH₃, OCF₃, NHCH₃, SCH₃, SO₂CH₃, SO₂C₂H₅, COCH₃, COC₂H₅, CO₂CH₃, CO₂C₂H₅ or CH₂OCH₃;

R₆ is selected from H, Cl, Br, F, CN, NO₂, CO₂H, C(═O)NH₂, C(═O)NHCH₃, C(═O)N(CH₃)₂, CH₃, CF₃,

CF(CF₃)₂

OCF₃

OCH₂CF₃

OCF₂CHFCF₃

SO₂CH₃, SO₂C₂H₅

COCH₃, COC₂H₅, CO₂CH₃, CO₂C₂H₅

OPh, NHPh,

COPh

COCH₂Ph

CO₂Ph

CONHPh

pyridinoxy or 3-chloro-5-(trifluoromethyl)pyridin-2-yloxy;

But R₄, R₅, R₆, R₇ and R₈ can not be H simultaneously;

Or the salts formed from the compounds of general formula I with hydrochloric acid, sulfuric acid, phosphoric acid, trifluoroacetic acid, methylsulfonic acid or p-toluenesulfonic acid.

The terms used above to definite the compounds of general formula I represent substitutes as follow:

The “halogen” or “halo” is fluorine, chlorine, bromine or iodine.

The “alkyl” stands for straight or branched chain alkyl, such as methyl, ethyl, propyl, isopropyl or tert-butyl.

The “cycloalkyl” is substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl. The substitute(s) is(are) methyl, halogen, etc.

The “haloalkyl” stands for straight or branched chain alkyl, in which hydrogen atoms can be all or partly substituted with halogen, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc.

The “alkoxy” refers to straight or branched chain alkyl, which is linked to the structure by oxygen atom.

The “haloalkoxy” refers to straight or branched chain alkoxy, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc.

The “alkylthio” refers to straight or branched chain alkyl, which is linked to the structure by sulfur atom.

The “haloalkylthio” refers to straight or branched chain alkylthio, in which hydrogen atoms may be all or partly substituted with halogen, such as chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, etc.

The “alkylamino” refers to straight or branched chain alkyl, which is linked to the structure by nitrogen atom.

The “haloalkylamino” refers to straight or branched chain alkylamino, in which hydrogen atoms may be all or partly substituted with halogen.

The “alkenyl” refers to straight or branched chain alkenyl, such as ethenyl, 1-propenyl, 2-propenyl and different isomer of butenyl, pentenyl and hexenyl. Alkenyl also includes polyene, such as propa-1,2-dienyl and hexa-2,4-dienyl.

The “haloalkenyl” stands for straight or branched chain alkenyl, in which hydrogen atoms can be all or partly substituted with halogen.

The “alkynyl” refers to straight or branched chain alkynyl, such as ethynyl, 1-propynyl, 2-propynyl and different isomer of butynyl, pentynyl and hexynyl. Alkynyl also includes groups including more than one triple bonds, such as hexa-2,5-diynyl.

The “haloalkynyl” stands for straight or branched chain alkynyl, in which hydrogen atoms can be all or partly substituted with halogen.

The “aryl” and “aryl” in arylalkyl, aryloxy and aryloxyalkyl include phenyl or naphthyl, etc.

The “heteroaryl” stands for five member ring or six member ring containing one or more N, O, S hetero atoms. Such as furanyl, pyrazolyl, thiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, etc.

Part of the substitutes of R₁, R₂, R₄, R₅, R₆, R₇ and R₈ in formula I are separately listed in table 1, table 2, table 3, table 4 and table 5, but without being restricted thereby.

TABLE 1 substitute R₁ R₁ H CH₃ CH₂CH₃ CH₂CH₂CH₃ CH₂CH₂CH₂CH₃ COCH₃ COCH₂CH₃ COCH₂CH₂CH₃ CO₂CH₃ CO₂CH₂CH₃ COCH₂CO₂CH₃ CH₂CH═CH₂ CH₂CH₂CH═CF₂ CH₂C≡CH COCH═CH₂CO₂H COCH═CH₂CO₂CH₃ CO₂CH₃

CO₂CH₂CH₂CH₃ CONHCH₃ CONHCH₂CH₃ SO₂CH₃ SO₂CH₂CH₃ SCCl₃ CH₂OCH₃ CH₂CH₂OCH₃ CH₂CH₂OCH₂CH₃ CH₂CO₂CH₃ COCH₂CH₂CO₂CH₃ CH₂CH═CCl₂ CH₂CH₂CF═CF₂ CH₂C≡C—I

CH₂CO₂CH₂CH₃ COCH₂OCH₃ COCH₂OCH₂CH₃ SNHCH₃ SNHCH₂CH₃ SN(CH₃)₂ SN(CH₂CH₃)₂ COCH₂CO₂H COCH₂CH₂CO₂H COCHCH₃CO₂H COCHCH₃CO₂CH₃ CH₂CH═CF₂ CH₂CHF₂ CH₂C≡CCH₃

TABLE 2 substitute R₂ R₂ F Cl Br I CF₃ OCH₃ OCH₂CH₃ OCH(CH₃)₂

OCF₃ OCH₂CF₃ NHCH₃ N(CH₃)₂ NHCH₂CH₃ NH(CH₂)₂CH₃ NHCH(CH₃)₂ NHCH₂CF₃

SCH₃ SCH₂CH₃ SO₂CH₃ SO₂CH₂CH₃ OCH₂CH═CH₂ OCH₂CH═CCl₂ OCH₂C≡CH OCOCH₃ OCH₂Ph NHCH₂Ph OCOCH₂CH₃ NHCOCH₃ NHCOCH₂CH₃ OPh OPh-4-Cl OPh-2-Cl—4CF₃ OPh-2-Cl—4NO₂ NHPh NHPh-4-Cl NHPh-2-Cl—4CF₃

TABLE 3 substitute R₄(R₈) R₄(R₈) H F Cl Br I CN NO₂ CONH2 CONHCH₃ CON(CH₃)₂ CONHCH₂CH₃ CON(CH₂CH₃)₂ CONH(CH₂)₂CH₃ CONHCH(CH₃)₂ OCF₃ OH CH₃ CH₂CH₃ (CH₂)₂CH₃ CH(CH₃)₂ CF₃ CHF₂ CH₂F CH₂CF₃ CF₂CHF₂ CF₂CF₃ OCH₃ OCH₂CH₃ O(CH₂)₂CH₃ OCH(CH₃)₂ OCH₂CF₃ OCOCH₃ CH═CH₂ CH₂CH═CH₂ C≡CH CH₂C≡CH SO₂CH₃ SO₂CH₂CH₃ COCH₃ COCH₂CH₃ CO₂CH₃ CO₂CH₂CH₃ CH₂OCH₃ CH₂OCH₂CH₃ CH₂CO₂CH₃ CH₂CO₂CH₂CH₃ OCF₂CF₃ CO₂H Ph CH₂Ph OPh NHPh COPh CO₂Ph CO₂Ph-4-Cl CO₂Ph-2-Cl-4-CF₃ CO₂Ph-2-Cl-4-NO₂ CONHPh CONHPh-4-Cl CONHPh-2-Cl-4-CF₃ CONHPh-2-Cl-4-NO₂

TABLE 4 substitute R₅(R₇) R₅(R₇) H F Cl Br I CN NO₂ CONH₂ CONHCH₃ CON(CH₃)₂ CONHCH₂CH₃ CON(CH₂CH₃)₂ CONH(CH₂)₂CH₃ CONHCH(CH₃)₂ OSO₂CH₂CH₃ OCH₂OCH₃ OCH₂OCH₂CH₃ OCH₂CO₂CH₃ COPh OH CH₃ CH₂CH₃ (CH₂)₂CH₃ CH(CH₃)₂ CF₃ CHF₂ CH₂F CH₂CF₃ CF₂CHF₂ CF₂CF₃ OCH₃ OCH₂CH₃ O(CH₂)₂CH₃ OCH(CH₃)₂ Ph CH₂Ph OPh NHPh CONHPh CO₂H OCF₃ OCH₂CF₃ OCF₂CF₃ NHCH₃ NHCH₂CH₃ NHCH₂CF₃ SCH₃ SCH₂CH₃ CH═CH₂ CH₂CH═CH₂ C≡CH CH₂C≡CH SO₂CH₃ SO₂CH₂CH₃ CO₂Ph CO₂Ph-4-Cl CO₂Ph-2-Cl-4-CF₃ CO₂Ph-2-Cl-4-NO₂ COCH₂Ph COCH₂Ph-4-Cl COCH₃ COCH₂CH₃ CO₂CH₃ CO₂CH₂CH₃ CH₂OCH₃ CH₂OCH₂CH₃ CH₂CO₂CH₃ CH₂CO₂CH₂CH₃ OCOCH₃ OCOCH₂CH₃ OCO₂CH₃ OCO₂CH₂CH₃ OCONHCH₃ OCONHCH₂CH₃ OSO₂CH₃ CONHPh-4-Cl CONHPh-2-Cl-4-CF₃

TABLE 5 substitute R₆ R₆ H F Cl Br I CN NO₂ CONH₂ CONHCH₃ CON(CH₃)₂ CONHCH₂CH₃ CON(CH₂CH₃)₂ CONH(CH₂)₂CH₃ CO₂Ph CONHPh OH CONHCH(CH₃)₂ CH₃ CH₂CH₃ (CH₂)₂CH₃ CH(CH₃)₂ CF₃ CHF₂ CH₂F CH₂CF₃ CF₂CHF₂ CF₂CF₃ OCH₃ OCH₂CH₃ CO₂Ph-4-Cl CONHPh-4-Cl OCOCH₃ O(CH₂)₂CH₃ OCH(CH₃)₂ OCF₃ OCH₂CF₃ CH═CH₂ CH₂CH═CH₂ C≡CH CH₂C≡CH SO₂CH₃ SO₂CH₂CH₃ COCH₃ COCH₂CH₃ CO₂CH₃ CO₂Ph-2-Cl-4-CF₃ CONHPh-2-Cl-4-CF₃ CO₂H CO₂CH₂CH₃ CH₂OCH₃ CH₂OCH₂CH₃ CH₂CO₂CH₃ CH₂CO₂CH₂CH₃ OCH₂OCH₃ OCH₂OCH₂CH₃ Ph CH₂Ph OPh NHPh COPh COCH₂Ph

The present invention is also explained by the following compounds in Table 6, but without being restricted thereby.

TABLE 6 No. R₁ R₂ R₃ R₄ R₅ R₆ R₇ R₈  1 H Cl NO₂ F H F H H  2 H Cl NO₂ Cl H Cl H H  3 H Cl NO₂ Cl Cl Cl H H  4 H Cl NO₂ Cl H Cl Cl H  5 H Cl NO₂ Cl H Cl H Cl  6 H Cl NO₂ CN H H H H  7 H Cl NO₂ H H CN H H  8 H Cl NO₂ H H NO₂ H H  9 H Cl NO₂ NO₂ H NO₂ H H  10 H Cl NO₂ NO₂ H NO₂ H NO₂  11 H Cl NO₂ CF₃ H H H H  12 H Cl NO₂ H H CF₃ H H  13 H Cl NO₂ OCH₃ H H H H  14 H Cl NO₂ H H OCH₃ H H  15 H Cl NO₂ SCH₃ H H H H  16 H Cl NO₂ H H SCH₃ H H  17 H Cl NO₂ OCF₃ H H H H  18 H Cl NO₂ H H OCF₃ H H  19 H Cl NO₂ COCH₃ H H H H  20 H Cl NO₂ H H COCH₃ H H  21 H Cl NO₂ SO₂CH₃ H H H H  22 H Cl NO₂ H H SO₂CH₃ H H  23 H Cl NO₂ CO₂CH₃ H H H H  24 H Cl NO₂ H H CO₂CH₃ H H  25 H Cl NO₂ CONHPh H H H H  26 H Cl NO₂ H CONHPh H H H  27 H Cl NO₂ H H CONHPh H H  28 H Cl NO₂ CO₂Ph H H H H  29 H Cl NO₂ CONH₂ H H H H  30 H Cl NO₂ H H CONH₂ H H  31 H Cl NO₂ Cl H CF₃ H H  32 H Cl NO₂ Cl H NO₂ H H  33 H Cl NO₂ Cl H CN H H  34 H Cl NO₂ CH₃ H Cl H H  35 H Cl NO₂ CF₃ H Cl H H  36 H Cl NO₂ NO₂ H Cl H H  37 H Cl NO₂ CN H Cl H H  38 H Cl NO₂ Cl H Cl H NO₂  39 H Cl NO₂ Cl H Cl H CN  40 H Cl NO₂ Cl H Cl H CF₃  41 H Cl NO₂ F H F H NO₂  42 H Cl NO₂ F H NO₂ H F  43 H Cl NO₂ Cl H NO₂ H Cl  44 H Cl NO₂ Cl H CF₃ H Cl  45 H Cl NO₂ Cl H CN H Cl  46 H Cl NO₂ Cl H COCH₃ H Cl  47 H Cl NO₂ Cl H CONH₂ H Cl  48 H Cl NO₂ NO₂ H F H H  49 H Cl NO₂ NO₂ H Br H H  50 H Cl NO₂ NO₂ H CF₃ H H  51 H Cl NO₂ NO₂ H CN H H  52 H Cl NO₂ NO₂ H COCH₃ H H  53 H Cl NO₂ NO₂ H CONH₂ H H  54 H Cl NO₂ NO₂ H CH₃ H H  55 H Cl NO₂ CF₃ H NO₂ H H  56 H Cl NO₂ CN H NO₂ H H  57 H Cl NO₂ COCH₃ H NO₂ H H  58 H Cl NO₂ CONH₂ H NO₂ H H  59 H Cl NO₂ CH₃ H NO₂ H H  60 H Cl NO₂ Cl H F H NO₂  61 H Cl NO₂ Cl H CF₃ H NO₂  62 H Cl NO₂ Cl H NO₂ H NO₂  63 H Cl NO₂ Cl H CN H NO₂  64 H Cl NO₂ F H Cl H NO₂  65 H Cl NO₂ CH₃ H Cl H NO₂  66 H Cl NO₂ CF₃ H Cl H NO₂  67 H Cl NO₂ NO₂ H Cl H NO₂  68 H Cl NO₂ CN H Cl H NO₂  69 H Cl NO₂ NO₂ H CF₃ H NO₂  70 H Cl NO₂ NO₂ H CN H NO₂  71 H Cl NO₂ NO₂ H CH₃ H NO₂  72 H Cl NO₂ NO₂ H F H NO₂  73 H Cl NO₂ CF₃ H NO₂ H NO₂  74 H Cl NO₂ CN H NO₂ H NO₂  75 H Cl NO₂ CH₃ H NO₂ H NO₂  76 H Cl NO₂ F H NO₂ H NO₂  77 H Cl NO₂ H CF₃ CN H H  78 H Cl NO₂ NO₂ H CN CF₃ H  79 H Cl NO₂ Br H OCF₃ H Br  80 H Cl NO₂ CH₃ H Cl CH₂CO₂ H C₂H₅  81 H Cl NO₂ Cl CH₃ Cl H H  82 H Cl NO₂ Cl CH₃ Cl H NO₂  83 H Cl NO₂ Cl CH₃ H H H  84 H Cl NO₂ CH₃ Cl H H H  85 H Cl NO₂ CH₃ Cl NO₂ H NO₂  86 H Cl NO₂ CH₃ Cl NO₂ H H  87 H Cl NO₂ Cl CH₃ NO₂ H NO₂  88 H Cl NO₂ Br H NO₂ H CN  89 H Cl NO₂ NO₂ Cl CF₃ H NO₂  90 H Cl NO₂ NO₂ H Cl Cl H  91 H Cl NO₂ Cl H NO₂ Cl H  92 H Cl NO₂ Cl H H Cl NO₂  93 H Cl NO₂ Cl Cl NO₂ H H  94 H Cl NO₂ Cl Cl H H NO₂  95 H Cl NO₂ NO₂ Cl Cl H NO₂  96 H Cl NO₂ Cl H NO₂ Cl NO₂  97 H Cl NO₂ Cl H Cl Cl NO₂  98 H Cl NO₂ Cl Cl Cl NO₂ H  99 H Cl NO₂ Cl Cl Cl H NO₂ 100 H Cl NO₂ Cl Cl NO₂ Cl NO₂ 101 H Cl NO₂ Cl H OCF₂CHFCF₃ Cl H 102 H Cl NO₂ H Cl

Cl H 103 H Cl H F H F H H 104 H Cl H Cl H Cl H H 105 H Cl H Cl Cl Cl H H 106 H Cl H Cl H Cl Cl H 107 H Cl H Cl H Cl H Cl 108 H Cl H CN H H H H 109 H Cl H H H CN H H 110 H Cl H H H NO₂ H H 111 H Cl H NO₂ H NO₂ H H 112 H Cl H NO₂ H NO₂ H NO₂ 113 H Cl H H H CF₃ H H 114 H Cl H Cl H NO₂ H H 115 H Cl H Cl H CN H H 116 H Cl H CH₃ H Cl H H 117 H Cl H NO₂ H Cl H H 118 H Cl H CN H Cl H H 119 H Cl H Cl H NO₂ H Cl 120 H Cl H Cl H CF₃ H Cl 121 H Cl H Cl H CN H Cl 122 H Cl H Cl H Cl H NO₂ 123 H Cl H Cl H Cl H CN 124 H Cl H Cl H Cl H CF₃ 125 H Cl H F H F H NO₂ 126 H Cl H NO₂ H CN H H 127 H Cl H Cl H CF₃ H NO₂ 128 H Cl H Cl H NO₂ H NO₂ 129 H Cl H Cl H CN H NO₂ 130 H Cl H CH₃ H Cl H NO₂ 131 H Cl H NO₂ H Cl H NO₂ 132 H Cl H NO₂ H CF₃ H NO₂ 133 H Cl H NO₂ H CN H NO₂ 134 H Cl H CF₃ H NO₂ H NO₂ 135 H Cl H CH₃ H NO₂ H NO₂ 136 H Cl H H CF₃ CN H H 137 H Cl H NO₂ H CN CF₃ H 138 H Cl H Br H OCF₃ H Br 139 H Cl H CH₃ H Cl CH₂CO₂ H C₂H₅ 140 H Cl H Cl CH₃ Cl H H 141 H Cl H Cl CH₃ Cl H NO₂ 142 H Cl H Cl CH₃ H H H 143 H Cl H CH₃ Cl H H H 144 H Cl H CH₃ Cl NO₂ H H 145 H Cl H Br H NO₂ H CN 146 H Cl H NO₂ Cl CF₃ H NO₂ 147 H Cl H NO₂ H Cl Cl H 148 H Cl H Cl H NO₂ Cl H 149 H Cl H NO₂ Cl Cl H NO₂ 150 H Cl H Cl H NO₂ Cl NO₂ 151 H Cl H Cl H Cl Cl NO₂ 152 H Cl H Cl Cl CN Cl CN 153 H Cl H Cl H OCF₂OCF₃ Cl H 154 H Cl CN Cl H NO₂ H Cl 155 H Cl CN Cl H CF₃ H Cl 156 H Cl CN Cl H CN H Cl 157 H Cl CN NO₂ H CF₃ H NO₂ 158 H Cl CN Cl H Cl H Cl 159 H Cl CN NO₂ H Cl H NO₂ 160 H Cl CN Br H NO₂ H CN 161 H Cl CN NO₂ H CN CF₃ H 162 H Cl CN Cl H NO₂ Cl H 163 H Cl CN Cl H NO₂ Cl NO₂ 164 H Cl CN Cl H Cl Cl NO₂ 165 H Cl CN NO₂ H NO₂ H H 166 H Cl CN Cl H NO₂ H NO₂ 167 H Cl CN Cl H CN H NO₂ 168 H Cl CN Cl H Cl H NO₂ 169 H Cl CN Cl H Cl H CN 170 H Cl CN Cl H Cl H CF₃ 171 H Cl Cl Cl H NO₂ H Cl 172 H Cl Cl Cl H CF₃ H Cl 173 H Cl Cl Cl H CN H Cl 174 H Cl Cl NO₂ H CF₃ H NO₂ 175 H Cl Cl Cl H Cl H Cl 176 H Cl Cl NO₂ H Cl H NO₂ 177 H Cl Cl Br H NO₂ H CN 178 H Cl Cl NO₂ H CN CF₃ H 179 H Cl Cl Cl H NO₂ Cl H 180 H Cl Cl Cl H NO₂ Cl NO₂ 181 H Cl Cl Cl H Cl Cl NO₂ 182 H Cl Cl NO₂ H NO₂ H H 183 H Cl Cl Cl H NO₂ H NO₂ 184 H Cl Cl Cl H CN H NO₂ 185 H Cl Cl Cl H Cl H NO₂ 186 H Cl Cl Cl H Cl H CN 187 H Cl Cl Cl H Cl H CF₃ 188 H Cl C(═O)NH₂ Cl H NO₂ H Cl 189 H Cl C(═O)NH₂ Cl H CF₃ H Cl 190 H Cl C(═O)NH₂ Cl H CN H Cl 191 H Cl C(═O)NH₂ NO₂ H CF₃ H NO₂ 192 H Cl C(═O)NH₂ Cl H Cl H Cl 193 H Cl C(═O)NH₂ NO₂ H Cl H NO₂ 194 H Cl C(═0)NH₂ Br H NO₂ H CN 195 H Cl C(═O)NH₂ NO₂ H CN CF₃ H 196 H Cl C(═O)NH₂ Cl H NO₂ Cl H 197 H Cl C(═O)NH₂ Cl H NO₂ Cl NO₂ 198 H Cl C(═O)NH₂ Cl H Cl Cl NO₂ 199 H Cl C(═O)NH₂ NO₂ H NO₂ H H 200 H Cl C(═O)NH₂ Cl H NO₂ H NO₂ 201 H Cl C(═O)NH₂ Cl H CN H NO₂ 202 H Cl C(═O)NH₂ Cl H Cl H NO₂ 203 H Cl C(═O)NH₂ Cl H Cl H CN 204 H Cl C(═O)NH₂ Cl H Cl H CF₃ 205 H Cl C(═S)NH₂ Cl H NO₂ H Cl 206 H Cl C(═S)NH₂ Cl H CF₃ H Cl 207 H Cl C(═S )NH₂ Cl H CN H Cl 208 H Cl C(═S)NH₂ NO₂ H CF₃ H NO₂ 209 H Cl C(═S)NH₂ Cl H Cl H Cl 210 H Cl C(═S)NH₂ NO₂ H Cl H NO₂ 211 H Cl C(═S)NH₂ Br H NO₂ H CN 212 H Cl C(═S)NH₂ NO₂ H CN CF₃ H 213 H Cl C(═S)NH₂ Cl H NO₂ Cl H 214 H Cl C(═S )NH₂ Cl H NO₂ Cl NO₂ 215 H Cl C(═S)NH₂ Cl H Cl Cl NO₂ 216 H Cl C(═S)NH₂ NO₂ H NO₂ H H 217 H Cl C(═S)NH₂ Cl H NO₂ H NO₂ 218 H Cl C(═S)NH₂ Cl H CN H NO₂ 219 H Cl C(═S)NH₂ Cl H Cl H NO₂ 220 H Cl C(═S)NH₂ Cl H Cl H CN 221 H Cl C(═S)NH₂ Cl H Cl H CF₃ 222 H Cl CO₂CH₃ Cl H NO₂ H Cl 223 H Cl CO₂CH₃ Cl H CF₃ H Cl 224 H Cl CO₂CH₃ Cl H CN H Cl 225 H Cl CO₂CH₃ NO₂ H CF₃ H NO₂ 226 H Cl CO₂CH₃ Cl H Cl H Cl 227 H Cl CO₂CH₃ NO₂ H Cl H NO₂ 228 H Cl CO₂CH₃ Br H NO₂ H CN 229 H Cl CO₂CH₃ NO₂ H CN CF₃ H 230 H Cl CO₂CH₃ Cl H NO₂ Cl H 231 H Cl CO₂CH₃ Cl H NO₂ Cl NO₂ 232 H Cl CO₂CH₃ Cl H Cl Cl NO₂ 233 H Cl CO₂CH₃ NO₂ H NO₂ H H 234 H Cl CO₂CH₃ Cl H NO₂ H NO₂ 235 H Cl CO₂CH₃ Cl H CN H NO₂ 236 H Cl CO₂CH₃ Cl H Cl H NO₂ 237 H Cl CO₂CH₃ Cl H Cl H CN 238 H Cl CO₂CH₃ Cl H Cl H CF₃ 239 H Cl CF₃ Cl H NO₂ H Cl 240 H Cl CF₃ Cl H CF₃ H Cl 241 H Cl CF₃ Cl H CN H Cl 242 H Cl CF₃ NO₂ H CF₃ H NO₂ 243 H Cl CF₃ Cl H Cl H Cl 244 H Cl CF₃ NO₂ H Cl H NO₂ 245 H Cl CF₃ Br H NO₂ H CN 246 H Cl CF₃ NO₂ H CN CF₃ H 247 H Cl CF₃ Cl H NO₂ Cl H 248 H Cl CF₃ Cl H NO₂ Cl NO₂ 249 H Cl CF₃ Cl H Cl Cl NO₂ 250 H Cl CF₃ NO₂ H NO₂ H H 251 H Cl CF₃ Cl H NO₂ H NO₂ 252 H Cl CF₃ Cl H CN H NO₂ 253 H Cl CF₃ Cl H Cl H NO₂ 254 H Cl CF₃ Cl H Cl H CN 255 H Cl CF₃ Cl H Cl H CF₃ 256 H Cl SO₂CH₃ Cl H NO₂ H Cl 257 H Cl SO₂CH₃ Cl H CF₃ H Cl 258 H Cl SO₂CH₃ Cl H CN H Cl 259 H Cl SO₂CH₃ NO₂ H CF₃ H NO₂ 260 H Cl SO₂CH₃ Cl H Cl H Cl 261 H Cl SO₂CH₃ NO₂ H Cl H NO₂ 262 H Cl SO₂CH₃ Br H NO₂ H CN 263 H Cl SO₂CH₃ NO₂ H CN CF₃ H 264 H Cl SO₂CH₃ Cl H NO₂ Cl H 265 H Cl SO₂CH₃ Cl H NO₂ Cl NO₂ 266 H Cl SO₂CH₃ Cl H Cl Cl NO₂ 267 H Cl SO₂CH₃ NO₂ H NO₂ H H 268 H Cl SO₂CH₃ Cl H NO₂ H NO₂ 269 H Cl SO₂CH₃ Cl H CN H NO₂ 270 H Cl SO₂CH₃ Cl H Cl H NO₂ 271 H Cl SO₂CH₃ Cl H Cl H CN 272 H Cl SO₂CH₃ Cl H Cl H CF₃ 273 CH₃ Cl NO₂ Cl H NO₂ H Cl 274 CH₃ Cl NO₂ Cl H CF₃ H Cl 275 CH₃ Cl NO₂ Cl H CN H Cl 276 CH₃ Cl NO₂ NO₂ H CF₃ H NO₂ 277 CH₃ Cl NO₂ Cl H Cl H Cl 278 CH₃ Cl NO₂ NO₂ H Cl H NO₂ 279 CH₃ Cl NO₂ Br H NO₂ H CN 280 CH₃ Cl NO₂ NO₂ H CN CF₃ H 281 CH₃ Cl NO₂ Cl H NO₂ Cl H 282 CH₃ Cl NO₂ Cl H NO₂ Cl NO₂ 283 CH₃ Cl NO₂ Cl H Cl Cl NO₂ 284 CH₃ Cl NO₂ NO₂ H NO₂ H H 285 CH₃ Cl NO₂ Cl H Cl H H 286 CH₃ Cl NO₂ Cl H NO₂ H NO₂ 287 CH₃ Cl NO₂ Cl H CN H NO₂ 288 CH₃ Cl NO₂ Cl H Cl H NO₂ 289 CH₃ Cl NO₂ Cl H Cl H CN 290 CH₃ Cl NO₂ Cl H Cl H CF₃ 291 CH₃ Cl NO₂ Br H NO₂ H Br 292 CH₃ Cl NO₂ F H NO₂ H F 293 CH₃ Cl NO₂ Cl H NO₂ H Br 294 CH₃ Cl NO₂ F H NO₂ H Cl 295 CH₃ Cl NO₂ F H NO₂ H Br 296 COCH₃ Cl NO₂ Cl H NO₂ H Cl 297 COCH₃ Cl NO₂ Cl H CF₃ H Cl 298 COCH₃ Cl NO₂ Cl H CN H Cl 299 COCH₃ Cl NO₂ NO₂ H CF₃ H NO₂ 300 COCH₃ Cl NO₂ Cl H Cl H Cl 301 COCH₃ Cl NO₂ NO₂ H Cl H NO₂ 302 COCH₃ Cl NO₂ Br H NO₂ H CN 303 COCH₃ Cl NO₂ NO₂ H CN CF₃ H 304 COCH₃ Cl NO₂ Cl H NO₂ Cl H 305 COCH₃ Cl NO₂ Cl H NO₂ Cl NO₂ 306 COCH₃ Cl NO₂ Cl H Cl Cl NO₂ 307 COCH₃ Cl NO₂ NO₂ H NO₂ H H 308 COCH₃ Cl NO₂ Cl H NO₂ H NO₂ 309 COCH₃ Cl NO₂ Cl H CN H NO₂ 310 COCH₃ Cl NO₂ Cl H Cl H NO₂ 311 COCH₃ Cl NO₂ Cl H Cl H CN 312 COCH₃ Cl NO₂ Cl H Cl H CF₃ 313 CO₂CH₃ Cl NO₂ Cl H NO₂ H Cl 314 CO₂CH₃ Cl NO₂ Cl H CF₃ H Cl 315 CO₂CH₃ Cl NO₂ Cl H CN H Cl 316 CO₂CH₃ Cl NO₂ NO₂ H CF₃ H NO₂ 317 CO₂CH₃ Cl NO₂ Cl H Cl H Cl 318 CO₂CH₃ Cl NO₂ NO₂ H Cl H NO₂ 319 CO₂CH₃ Cl NO₂ Br H NO₂ H CN 320 CO₂CH₃ Cl NO₂ NO₂ H CN CF₃ H 321 CO₂CH₃ Cl NO₂ Cl H NO₂ Cl H 322 CO₂CH₃ Cl NO₂ Cl H NO₂ Cl NO₂ 323 CO₂CH₃ Cl NO₂ Cl H Cl Cl NO₂ 324 CO₂CH₃ Cl NO₂ NO₂ H NO₂ H H 325 CO₂CH₃ Cl NO₂ Cl H NO₂ H NO₂ 326 CO₂CH₃ Cl NO₂ Cl H CN H NO₂ 327 CO₂CH₃ Cl NO₂ Cl H Cl H NO₂ 328 CO₂CH₃ Cl NO₂ Cl H Cl H CN 329 CO₂CH₃ Cl NO₂ Cl H Cl H CF₃ 330 SO₂CH₃ Cl NO₂ Cl H NO₂ H Cl 331 SO₂CH₃ Cl NO₂ Cl H CF₃ H Cl 332 SO₂CH₃ Cl NO₂ Cl H CN H Cl 333 SO₂CH₃ Cl NO₂ NO₂ H CF₃ H NO₂ 334 SO₂CH₃ Cl NO₂ Cl H Cl H Cl 335 SO₂CH₃ Cl NO₂ NO₂ H Cl H NO₂ 336 SO₂CH₃ Cl NO₂ Br H NO₂ H CN 337 SO₂CH₃ Cl NO₂ NO₂ H CN CF₃ H 338 SO₂CH₃ Cl NO₂ Cl H NO₂ Cl H 339 SO₂CH₃ Cl NO₂ Cl H NO₂ Cl NO₂ 340 SO₂CH₃ Cl NO₂ Cl H Cl Cl NO₂ 341 SO₂CH₃ Cl NO₂ NO₂ H NO₂ H H 342 SO₂CH₃ Cl NO₂ Cl H NO₂ H NO₂ 343 SO₂CH₃ Cl NO₂ Cl H CN H NO₂ 344 SO₂CH₃ Cl NO₂ Cl H Cl H NO₂ 345 SO₂CH₃ Cl NO₂ Cl H Cl H CN 346 SO₂CH₃ Cl NO₂ Cl H Cl H CF₃ 347 H OCH₃ NO₂ Cl H NO₂ H Cl 348 H OCH₃ NO₂ Cl H CF₃ H Cl 349 H OCH₃ NO₂ Cl H CN H Cl 350 H OCH₃ NO₂ NO₂ H CF₃ H NO₂ 351 H OCH₃ NO₂ Cl H Cl H Cl 352 H OCH₃ NO₂ NO₂ H Cl H NO₂ 353 H OCH₃ NO₂ Br H NO₂ H CN 354 H OCH₃ NO₂ NO₂ H CN CF₃ H 355 H OCH₃ NO₂ Cl H NO₂ Cl H 356 H OCH₃ NO₂ Cl H NO₂ Cl NO₂ 357 H OCH₃ NO₂ Cl H Cl Cl NO₂ 358 H OCH₃ NO₂ NO₂ H NO₂ H H 359 H OCH₃ NO₂ Cl H NO₂ H NO₂ 360 H OCH₃ NO₂ Cl H CN H NO₂ 361 H OCH₃ NO₂ Cl H Cl H NO₂ 362 H OCH₃ NO₂ Cl H Cl H CN 363 H OCH₃ NO₂ Cl H Cl H CF₃ 364 H OCH₃ NO₂ Br H NO₂ H Br 365 H OCH₃ NO₂ F H NO₂ H F 366 H OCH₃ NO₂ Cl H NO₂ H Br 367 H OCH₃ NO₂ F H NO₂ H Cl 368 H OCH₃ NO₂ F H NO₂ H Br 369 H SCH₃ NO₂ Cl H NO₂ H Cl 370 H SCH₃ NO₂ Cl H CF₃ H Cl 371 H SCH₃ NO₂ Cl H CN H Cl 372 H SCH₃ NO₂ NO₂ H CF₃ H NO₂ 373 H SCH₃ NO₂ Cl H Cl H Cl 374 H SCH₃ NO₂ NO₂ H Cl H NO₂ 375 H SCH₃ NO₂ Br H NO₂ H CN 376 H SCH₃ NO₂ NO₂ H CN CF₃ H 377 H SCH₃ NO₂ Cl H NO₂ Cl H 378 H SCH₃ NO₂ Cl H NO₂ Cl NO₂ 379 H SCH₃ NO₂ Cl H Cl Cl NO₂ 380 H SCH₃ NO₂ NO₂ H NO₂ H H 381 H SCH₃ NO₂ Cl H NO₂ H NO₂ 382 H SCH₃ NO₂ Cl H CN H NO₂ 383 H SCH₃ NO₂ Cl H Cl H NO₂ 384 H SCH₃ NO₂ Cl H Cl H CN 385 H SCH₃ NO₂ Cl H Cl H CF₃ 386 H SCH₃ NO₂ Br H NO₂ H Br 387 H SCH₃ NO₂ F H NO₂ H F 388 H SCH₃ NO₂ Cl H NO₂ H Br 389 H SCH₃ NO₂ F H NO₂ H Cl 390 H SCH₃ NO₂ F H NO₂ H Br 391 H NHCH₃ NO₂ Cl H NO₂ H Cl 392 H NHCH₃ NO₂ Cl H CF₃ H Cl 393 H NHCH₃ NO₂ Cl H CN H Cl 394 H NHCH₃ NO₂ NO₂ H CF₃ H NO₂ 395 H NHCH₃ NO₂ Cl H Cl H Cl 396 H NHCH₃ NO₂ NO₂ H Cl H NO₂ 397 H NHCH₃ NO₂ Br H NO₂ H CN 398 H NHCH₃ NO₂ NO₂ H CN CF₃ H 399 H NHCH₃ NO₂ Cl H NO₂ Cl H 400 H NHCH₃ NO₂ Cl H NO₂ Cl NO₂ 401 H NHCH₃ NO₂ Cl H Cl Cl NO₂ 402 H NHCH₃ NO₂ NO₂ H NO₂ H H 403 H NHCH₃ NO₂ Cl H NO₂ H NO₂ 404 H NHCH₃ NO₂ Cl H CN H NO₂ 405 H NHCH₃ NO₂ Cl H Cl H NO₂ 406 H NHCH₃ NO₂ Cl H Cl H CN 407 H NHCH₃ NO₂ Cl H Cl H CF₃ 408 H NHCH₃ NO₂ Br H NO₂ H Br 409 H NHCH₃ NO₂ F H NO₂ H F 410 H NHCH₃ NO₂ Cl H NO₂ H Br 411 H NHCH₃ NO₂ F H NO₂ H Cl 412 H NHCH₃ NO₂ F H NO₂ H Br 413 H N(CH₃)₂ NO₂ Cl H NO₂ H Cl 414 H N(CH₃)₂ NO₂ Cl H CF₃ H Cl 415 H N(CH₃)₂ NO₂ Cl H CN H Cl 416 H N(CH₃)₂ NO₂ NO₂ H CF₃ H NO₂ 417 H N(CH₃)₂ NO₂ Cl H Cl H Cl 418 H N(CH₃)₂ NO₂ NO₂ H Cl H NO₂ 419 H N(CH₃)₂ NO₂ Br H NO₂ H CN 420 H N(CH₃)₂ NO₂ NO₂ H CN CF₃ H 421 H N(CH₃)₂ NO₂ Cl H NO₂ Cl H 422 H N(CH₃)₂ NO₂ Cl H NO₂ Cl NO₂ 423 H N(CH₃)₂ NO₂ Cl H Cl Cl NO₂ 424 H N(CH₃)₂ NO₂ NO₂ H NO₂ H H 425 H N(CH₃)₂ NO₂ Cl H NO₂ H NO₂ 426 H N(CH₃)₂ NO₂ Cl H CN H NO₂ 427 H N(CH₃)₂ NO₂ Cl H Cl H NO₂ 428 H N(CH₃)₂ NO₂ Cl H Cl H CN 429 H N(CH₃)₂ NO₂ Cl H Cl H CF₃ 430 H N(CH₃)₂ NO₂ Br H NO₂ H Br 431 H N(CH₃)₂ NO₂ F H NO₂ H F 432 H N(CH₃)₂ NO₂ Cl H NO₂ H Br 433 H N(CH₃)₂ NO₂ F H NO₂ H Cl 434 H N(CH₃)₂ NO₂ F H NO₂ H Br 435 H OPh NO₂ Cl H NO₂ H Cl 436 H OPh NO₂ Cl H CF₃ H Cl 437 H OPh NO₂ Cl H CN H Cl 438 H OPh NO₂ NO₂ H CF₃ H NO₂ 439 H OPh NO₂ Cl H Cl H Cl 440 H OPh NO₂ NO₂ H Cl H NO₂ 441 H OPh NO₂ Br H NO₂ H CN 442 H OPh NO₂ NO₂ H CN CF₃ H 443 H OPh NO₂ Cl H NO₂ Cl H 444 H OPh NO₂ Cl H NO₂ Cl NO₂ 445 H OPh NO₂ Cl H Cl Cl NO₂ 446 H OPh NO₂ NO₂ H NO₂ H H 447 H OPh NO₂ Cl H NO₂ H NO₂ 448 H OPh NO₂ Cl H CN H NO₂ 449 H OPh NO₂ Cl H Cl H NO₂ 450 H OPh NO₂ Cl H Cl H CN 451 H OPh NO₂ Cl H Cl H CF₃ 452 H OPh NO₂ Br H NO₂ H Br 453 H OPh NO₂ F H NO₂ H F 454 H OPh NO₂ Cl H NO₂ H Br 455 H OPh NO₂ F H NO₂ H Cl 456 H OPh NO₂ F H NO₂ H Br 457 H OCH₂CF₃ NO₂ Cl H NO₂ H Cl 458 H OCH₂CF₃ NO₂ Cl H CF₃ H Cl 459 H OCH₂CF₃ NO₂ Cl H CN H Cl 460 H OCH₂CF₃ NO₂ NO₂ H CF₃ H NO₂ 461 H OCH₂CF₃ NO₂ Cl H Cl H Cl 462 H OCH₂CF₃ NO₂ NO₂ H Cl H NO₂ 463 H OCH₂CF₃ NO₂ Br H NO₂ H CN 464 H OCH₂CF₃ NO₂ NO₂ H CN CF₃ H 465 H OCH₂CF₃ NO₂ Cl H NO₂ Cl H 466 H OCH₂CF₃ NO₂ Cl H NO₂ Cl NO₂ 467 H OCH₂CF₃ NO₂ Cl H Cl Cl NO₂ 468 H OCH₂CF₃ NO₂ NO₂ H NO₂ H H 469 H OCH₂CF₃ NO₂ Cl H NO₂ H NO₂ 470 H OCH₂CF₃ NO₂ Cl H CN H NO₂ 471 H OCH₂CF₃ NO₂ Cl H Cl H NO₂ 472 H OCH₂CF₃ NO₂ Cl H Cl H CN 473 H OCH₂CF₃ NO₂ Cl H Cl H CF₃ 474 H OCH₂CF₃ NO₂ Br H NO₂ H Br 475 H OCH₂CF₃ NO₂ F H NO₂ H F 476 H OCH₂CF₃ NO₂ Cl H NO₂ H Br 477 H OCH₂CF₃ NO₂ F H NO₂ H Cl 478 H OCH₂CF₃ NO₂ F H NO₂ H Br 479 H NHCH₂CF₃ NO₂ Cl H NO₂ H Cl 480 H NHCH₂CF₃ NO₂ Cl H CF₃ H Cl 481 H NHCH₂CF₃ NO₂ Cl H CN H Cl 482 H NHCH₂CF₃ NO₂ NO₂ H CF₃ H NO₂ 483 H NHCH₂CF₃ NO₂ Cl H Cl H Cl 484 H NHCH₂CF₃ NO₂ NO₂ H Cl H NO₂ 485 H NHCH₂CF₃ NO₂ Br H NO₂ H CN 486 H NHCH₂CF₃ NO₂ NO₂ H CN CF₃ H 487 H NHCH₂CF₃ NO₂ Cl H NO₂ Cl H 488 H NHCH₂CF₃ NO₂ Cl H NO₂ Cl NO₂ 489 H NHCH₂CF₃ NO₂ Cl H Cl Cl NO₂ 490 H NHCH₂CF₃ NO₂ NO₂ H NO₂ H H 491 H NHCH₂CF₃ NO₂ Cl H NO₂ H NO₂ 492 H NHCH₂CF₃ NO₂ Cl H CN H NO₂ 493 H NHCH₂CF₃ NO₂ Cl H Cl H NO₂ 494 H NHCH₂CF₃ NO₂ Cl H Cl H CN 495 H NHCH₂CF₃ NO₂ Cl H Cl H CF₃ 496 H NHCH₂CF₃ NO₂ Br H NO₂ H Br 497 H NHCH₂CF₃ NO₂ F H NO₂ H F 498 H NHCH₂CF₃ NO₂ Cl H NO₂ H Br 499 H NHCH₂CF₃ NO₂ F H NO₂ H Cl 500 H NHCH₂CF₃ NO₂ F H NO₂ H Br 501 H Cl NO₂ Cl H NO₂ H Br 502 H Cl NO₂ Br H NO₂ H Br 503 H Cl NO₂ Cl H CO₂CH₃ H Cl 504 H Cl NO₂ F H NO₂ H Cl 505 H Cl NO₂ F H H H F 506 H Cl NO₂ F H Cl H F 507 CH₃ Cl NO₂ NO₂ H NO₂ H NO₂ 508 H Cl NO₂ Cl H CONHCH₃ H Cl 509 H NHCH₃ NO₂ Cl H CONHCH₃ H Cl 510 CH₃ Cl NO₂ Cl H CF₃ H H 511 H Cl NO₂ Cl H COOH H Cl 512 CH₂CH═CH₂ Cl NO₂ Cl H NO₂ H Cl 513 CH₂CH═CCl₂ Cl NO₂ Cl H NO₂ H Cl 514 CH₂CH═CF₂ Cl NO₂ Cl H NO₂ H Cl 515 (CH₂)₂CH═CF₂ Cl NO₂ Cl H NO₂ H Cl 516 (CH₂)₂CF═CF₂ Cl NO₂ Cl H NO₂ H Cl 517 CH₂CHF₂ Cl NO₂ Cl H NO₂ H Cl 518 CH₂C≡CH Cl NO₂ Cl H NO₂ H Cl 519 CH₂C≡C—I Cl NO₂ Cl H NO₂ H Cl 520 CH₂C≡CH₃ Cl NO₂ Cl H NO₂ H Cl 521 H Cl NO₂ CH₃ H H H Cl 522 H Cl NO₂ CH₃ H NO₂ H Cl 523 H Cl NO₂ CH₃ H NO₂ H Br 524 H Cl NO₂ CH₃ H NO₂ H F

The technical scheme of the present invention also includes the preparation method of the compounds, and the reaction formula is as follow:

Wherein: X and Y are different, separately selected from halogen atom or amino; Z is halogen atom; R₂, R₃, R₄, R₅, R₆, R₇ and R₈ are defined respectively as mentioned before; R₁ are defined as mentioned before, but R₁≠H.

According to the above preparation method, treatment of intermediate II with intermediate III at the presence of base gives compounds I-a of general formula I (R₁=H), which react with Z—R₁ to give compounds I-b of general formula I (R₁≠H).

The proper base mentioned above may be selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide and so on.

The reaction can be carried out in proper solvent, and the proper solvent mentioned may be selected from tetrahydrofuran, acetonitrile, toluene, xylene, benzene, DMF, N-methylpyrrolidone, DMSO, acetone or butanone and so on.

The proper reaction temperature is from room temperature to boiling point of solvent, generally is 20-100° C.

The reaction time is in the range of 30 minutes to 20 hours, generally is 1-10 hours.

Intermediates II are commercially available, or prepared according to the known methods, such as referring to Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 45B(4), 972-975, 2006; Tetrahedron Letters, 44(21), 4085-4088, 2003; PL174903, etc.

Intermediate III can be prepared according to the known methods, such as referring to JP2003292476, US2010160695, etc.

The compounds of general formula I can also be prepared by other methods, for example, the nitration of substituted diphenylamine intermediate (general formula IV) can give compounds of general formula I with NO₂ group, referring to US4041172 and so on.

Wherein: R₁, R₂, R₄, R₅, R₆, R₇ and R₈ are defined respectively as mentioned before; R₃ is selected from H or NO₂.

The nitration of compounds of general formula I, in which at least one of R₄, R₆ or R₈ is H, can add one or two NO₂ groups to these compounds of general formula I.

The halogenation of substituted diphenylamine compounds of general formula I, in which R₄, R₆ or R₈ is not halogen atom, can add one or two halogen atoms to these compounds of general formula I.

The compounds of general formula I, in which R₂ is alkylamino, alkoxy or alkylthio and so on, can be prepared from the reaction of compounds of general formula I whose R₂ is halogen atom with amine, alcohol or mercaptan (or their salts).

The salts of compounds having general formula I can be prepared from the reaction of the compounds of general formula I with corresponding acid according to routine method. The proper acid may be selected from hydrochloric acid, sulfuric acid, phosphoric acid, trifluoroacetic acid, methylsulfonic acid, p-toluenesulfonic acid, etc.

Although the compounds having general formula I of the present invention and some compounds reported in the prior art are all diphenylamine compounds, there are significant differences between their structural characteristics. And because of the structural differences, the compounds of the present invention show much better fungicidal activity. Meanwhile, the raw materials to prepare these compounds are cheap and the methods are simple and convenient, therefore the compounds of the present invention have lower costs and broader application prospect compared with known fungicides.

The compounds of general formula I show excellent activity against many plant pathogens/diseases in agricultural and other fields. Therefore the technical scheme of the present invention also include the uses of the compounds having general formula I to control plant pathogens/diseases in agricultural and other fields, such as using the compounds of general formula I to prepare substances to control plant pathogens/diseases.

The present invention is explained by the following examples of plant disease, but without being restricted thereby.

The compounds of general formula I can be used to control these plant diseases: Oomycete diseases, such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, downy mildew of beet, downy mildew of sugarcane, tobacco downy mildew, pea downy mildew, vegetable sponge downy mildew, chinese wax gourd downy mildew, muskmelon downy mildew, chinese cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew), white rust (rape white rust, chinese cabbage white rust), damping-off disease (rape damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton damping-off), pythium rot (pepper soft stale disease, vegetable sponge cottony leak, chinese wax gourd cottony leak), blight (broad bean phytophthora blight, cucumber phytophthora blight, pumpkin phytophthora rot, chinese wax gourd phytophthora blight, watermelon phytophthora blight, muskmelon phytophthora blight, pepper phytophthora blight, chinese chives phytophthora blight, carlic phytophthora blight, cotton phytophthora blight), late blight (potato late blight, tomato late blight) and so on; diseases caused by Deuteromycotina, such as wilt disease (sweet potato fusarium wilt, cotton fusarium wilt disease, sesame wilt disease, fusarium wilt disease of costarbean, tomato fusarium wilt, bean fusarium wilt, cucumber fusarium wilt, vegetable sponge fusarium wilt, pumpkin fusarium wilt, chinese wax gourd fusarium wilt, watermelon fusarium wilt, muskmelon fusarium wilt, pepper fusarium wilt, broad bean fusarium wilt, fusarium wilt disease of rape, fusarium wilt disease of soybean), root rot (pepper root rot, eggplant root rot, bean fusarium root-rot, cucumber fusarium root rot, balsam pear fusarium root rot, cotton black root rot, broad bean thielaviopsis root rot), drooping disease (cotton soreshin, sesame soreshin, pepper rhizoctonia rot, cucumber rhizoctonia rot, chinese cabbage rhizoctonia rot), anthracnose (sorghum anthracnose, cotton anthracnose, kenaf anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, mulberry anthracnose, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, balsam pear anthracnose, summer squash anthracnose, chinese wax gourd anthracnose, watermelon anthracnose, muskmelon anthracnose, litchi anthracnose), verticillium wilt (cotton verticillium wilt, verticillium wilt of sunflower, tomato verticillium wilt, pepper verticillium wilt, eggplant verticillium wilt), scab (summer squash scab, chinese wax gourd scab, muskmelon scab), gray mold (cotton boll gray mold, kenaf gray mold, tomato gray mold, pepper gray mold, bean gray mold, celery gray mold, spinach gray mold, kiwi fruit gray mold rot), brown spot (cotton brown spot, jute brown spot, beet sercospora leaf spot, peanut brown spot, pepper brown leaf spot, chinese wax gourd corynespora leaf spot, soybean brown spot, sunflower brown spot, pea ascochyta blight, broad bean brown spot), black spot (flax black spot, rape alternaria leaf spot, sesame black spot, sunflower alternaria leaf spot, costarbean alternaria leaf spot, tomato nail head spot, pepper black fruit spot, eggplant black spot, bean leaf spot, cucumber alternaria blight, celery alternaria black leaf spot, carrot alternaria black rot, carrot leaf blight, apple alternaria rot, peanut brown spot), spot blight (tomato septoria leaf spot, pepper septoria leaf spot, celery late blight), early blight (tomato early blight, pepper early blight, eggplant early blight, potato early blight, celery early blight), ring spot (soybean zonate spot, sesame ring spot, bean zonate spot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon alternaria blight, muskmelon alternaria spot), basal stem rot (tomato basal stem rot, bean rhizoctonia rot), and others (corn northern leaf spot, kenaf damping-off, rice blast, millet black sheath, sugarcane eye spot, cotton aspergillus boll rot, peanut crown rot, soybean stem blight, soybean black spot, muskmelon alternaria leaf blight, peanut web blotch, tea red leaf spot, pepper phyllosticta blight, chinese wax gourd phyllosticta leaf spot, celery black rot, spinach heart rot, kenaf leaf mold, kenaf brown leaf spot, Jute stem blight, soybean cercospora spot, sesame leaf spot, costarbean gray leaf spot, tea brown leaf spot, eggplant cercospora leaf spot, bean cercospora leaf spot, balsam pear cercospora leaf spot, watermelon cercospora leaf spot, jute dry rot, sunflower root and stem rot, bean charcoal rot, soybean target spot, eggplant corynespora leaf spot, cucumber corynespora target leaf spot, tomato leaf mold, eggplant fulvia leaf mold, broad bean chocolate spot) and so on; diseases caused by Basidiomycete, such as rust (wheat stripe rust, wheat stem rust, wheat leaf rust, peanut rust, sunflower rust, sugarcane rust, chinese chives rust, onion rust, millet rust, soybean rust), smut (corn head smut, corn smut, sorghum silk smut, sorghum loose kernel smut, sorghum hard smut, sorghum smut, millet kernel smut, sugarcane smut, bean rust), and others (for example, wheat sheath blight and rice sheath blight) and so on; diseases caused by Ascomycete, such as powdery mildew (wheat powdery mildew, rape powdery mildew, powdery mildew of sesame, powdery mildew of sunflower, beet powdery mildew, eggplant powdery mildew, pea powdery mildew, vegetable sponge powdery mildew, pumpkin powdery mildew, summer squash powdery mildew, chinese wax gourd, muskmelon powdery mildew, grape powdery mildew, broad bean powdery mildew), sclerotinia rot (flax sclertiniose, rape sclertiniose, soybean sclertiniose, peanut sclertiniose, tobacco sclerotinia rot, pepper sclerotinia rot, eggplant sclerotinia rot, bean sclerotinia rot, pea sclerotinia rot, cucumber sclerotinia rot, balsam pear sclerotinia rot, chinese wax gourd sclerotinia rot, watermelon sclerotinia disease, celery stem rot), scab (apple scab, pear scab) and so on. Especially, the compounds of the present invention exhibit very good control against cucumber downy mildew, rice blast and gray mold of vegetables at very low doses.

Thanks to their positive characteristics, the compounds mentioned above can be advantageously used in protecting crops of farming and gardening, domestic and breeding animals, as well as environments frequented by human beings, from pathogens.

In order to obtain desired effect, the dosage of the compound to be applied can vary with various factors, for example, the used compound, the protected crop, the type of harmful organism, the degree of infestation, the climatic conditions, the application method and the adopted formulation.

The dosage of compounds in the range of 10 g to 5 kg per hectare can provide a sufficient control.

An another object of the present invention also relates to a method for controlling phytopathogenic fungi in crops of farming and gardening and/or on domestic and breeding animals and/or environments frequented by human beings, by application of the compounds having general formula I. In particular, the dosage of compounds to be applied varies from 10 g to 5 kg per hectare.

For practical application in agriculture, it is usually beneficial to use compositions containing one or more compounds of general formula I.

Therefore, a further technical scheme of the present invention relates to fungicidal compositions containing one or more compounds having general formula I as active ingredient and acceptable carrier in agriculture, the weight percentage of the active ingredient in the compositions is 0.5-90%.

Compositions can be used in the form of dry powders, wettable powders, emulsifiable concentrates, microemulsions, pastes, granulates, solutions, suspensions, etc. The selection of the type of compositions depends on the specific application.

The compositions are prepared in the known method, for example by diluting or dissolving the active substance with a solvent medium and/or a solid diluent, optionally in the presence of surface-active agents.

Solid diluents or carriers which can be used are, for example: silica, kaolin, bentonite, talc, diatomite, dolomite, calcium carbonate, magnesia, chalk, clays, synthetic silicates, attapulgite, sepiolite.

Liquid diluents which can be used are, for example, besides water, aromatic organic solvents (xylols or mixtures of alkylbenzols, chlorobenzene, etc.), paraffins (petroleum fractions), alcohols (methanol, propanol, butanol, octanol, glycerin, etc.), esters (ethyl acetate, isobutyl acetate, etc.), ketones (cyclohexanone, acetone, acetophenone, isophorone, ethylamylketone, etc.), amides (N, N-dimethylformamide, N-methylpyrrolidone, etc.).

Surface-active agents which can be used are salts of sodium, calcium, triethylamine or triethanolamine of alkylsulfonates, alkylarylsulfonates, polyethoxylated alkylphenols, polyethoxylated esters of sorbitol, ligninsulfonates, etc.

The compositions can also contain special additives for particular purposes, for example adhesion agents such as Arabic gum, polyvinyl alcohol, polyvinyl-pyrrolidone, etc.

The concentration of active ingredient in the above compositions can vary within a wide range depending on the active compound, the applications for which they are destined, the environmental conditions and the type of adopted formulation. In general the concentration of active ingredient ranges from 1% to 90%, preferably from 5% to 50%.

If required, other active ingredients being compatible with the compounds having general formula I can be added to the compositions, such as, other acaricides/insecticides, fungicides, plant growth regulators, antibiotics, herbicides, fertilizers.

The preparation methods of several common formulation examples in the present invention are as follows:

The preparation of suspension concentrate: the common active component in formula is 5%-35%. With water as the medium, the compound in the invention, dispersing agent, suspending agent and antifreeze are added to sanding machine for grinding to make suspension concentrate.

The preparation of water emulsion: the compound in the invention, solvent and emulsifier are mixed together to make a homogeneous oil phase. The water is mixed with antifreeze to make a homogeneous aqueous phase. In the high-speed stirring, the aqueous phase is added to the oil phase or oil phase is added to the aqueous phase, forming the water emulsion with good dispersity. The active component of water emulsions is generally 5%−15% in this invention. For the production of concentrated emulsions, the compounds of this invention are dissolved in one or more of the mixed solvent, and then emulsifier was added to enhance dispersion effects in the water.

The preparation of wettable powder: according to formulation requirements, the compound in the invention, surfactants and solid diluents are mixed well, after smashing through ultrafine pulverizer, that is the wettable powder products (for example, 10%-40%). To prepare the spraying wettable powder, the compounds of this invention can form a mixture with solid powder, such as clay, inorganic silicates, carbonates, as well as wetting agents, adhesives and/or dispersant agent.

The preparation of water dispersible granules: the compound in the invention and powdered solid diluents, wetting agents and adhesives are mixed to smash, kneading together with water, added to the granulation machine with 10 to 100 mesh for granulation, then by drying and sieving (at the scope screen). Also, the compound of the invention, dispersants, disintegrants, wetting agents and solid diluent are added to sanding machine, grinding in water to produce suspension and then spray-drying granulation, usually the content of the prepared granular products is 20%-30%.

DETAILED DESCRIPTION OF THE INVENTION

The present invention is illustrated by the following examples, but without being restricted thereby. (All raw materials are commercially available unless otherwise specified.)

PREPARATION EXAMPLES Example 1 The Preparation of Compound 2

0.81 g (0.005 mol) of 2,4-dichloroaniline was added in portions to a suspension of 0.4 g (0.01 mol) of NaH (60%) and 20 mL of THF, the mixture was stirred for 30 min after addition, 1.56 g (0.006 mol) of 2,6-dichloro-3,5-dinitrotulune in 30 mL of THF was added within 30 min, then stirred for another 5 h. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure, then the residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1/20, as an eluent) to give 1.37 g of compound 2 as yellow solid, m.p. 136-137° C.

¹H-NMR spectrum (300 MHz, internal standard: TMS, solvent CDCl₃) δ (ppm): 2.14 (s, 3H), 6.53 (d, 1H), 7.17 (d, 1H), 7.49 (s, 1H), 8.68 (s, 1H), 8.93 (s, 1H).

Example 2 The Preparation of Compound 38

0.56 g (0.0015 mol) of compound 2 was dissolved in 5 mL of concentrated sulfuric acid (96%, the same below) and cooled to 0° C., 0.15 g of fuming nitric acid (95%) and 3 mL of concentrated sulfuric acid was mixed evenly and added to the flask, then the reaction mixture was stirred for another 5 min. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into ice water, the solid precipitated was filtered, and the filter mass was washed with water and dried to give 0.59 g of compound 38 as brown solid, m.p. 156-158° C.

¹H-NMR spectrum (300 MHz, internal standard: TMS, solvent CDCl₃) δ (ppm): 2.09 (s, 3H), 7.66 (s, 1H), 8.01 (s, 1H), 8.60 (s, 1H), 9.75 (s, 1H).

Example 3 The Preparation of Compound 43

0.83 g (0.004 mol) of 2,6-dichloro-4-nitroaniline was added in portions to a suspension of 0.32 g (0.008 mol) of NaH (60%) and 10 mL of DMF, the mixture was stirred for 30 min after addition, 1.20 g (0.0048 mol) of 2,6-dichloro-3,5-dinitrotulune was added in portions within 30 min, then stirred for another 3 h. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into 50 mL of saturated brine and extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1/10, as an eluent) to give 1.20 g of compound 43 as yellow solid, m.p. 157-158° C.

¹H-NMR spectrum (300 MHz, internal standard: TMS, solvent CDCl₃) δ (ppm): 2.02 (s, 3H), 8.29 (s, 2H), 8.65 (s, 1H), 8.95 (s, 1H).

Example 4 The Preparation of Compound 89

The intermediate M prepared by the procedure of Example 3 was nitrated according to Example 2 to give compound 89 as reddish-brown solid, m.p. 136-137° C.

¹H-NMR spectrum (300 MHz, internal standard: TMS, solvent CDCl₃) δ (ppm): 2.41 (s, 3H), 8.50 (s, 1H), 8.72 (s, 1H), 10.10 (s, 1H).

Example 5 The Preparation of Compound 285

0.38 g (0.001 mol) of compound 2 was added to a suspension of 0.10 g (0.0025 mol) of NaH (60%) and 10 mL of DMF, the mixture was stirred for 1 h and then added thereto 0.43 g (0.003 mol) of CH₃I, the resulting mixture was allowed to react for 5 h. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into 50 mL of saturated brine and extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)= 1/10, as an eluent) to give 0.15 g of compound 285 as yellow solid, m.p. 142-144° C.

¹H-NMR spectrum (300 MHz, internal standard: TMS, solvent CDCl₃) δ (ppm): 2.54 (s, 3H), 3.31 (s, 3H), 7.09 (d, 1H), 7.25 (d, 2H), 8.04 (s, 1H).

Example 6 The Preparation of Compound 391

0.42 g of compound 43 (0.001 mol) was added to a microwave vial and dissolved with 2.5 mL of DMSO, 1 mL of methylamine aqueous solution (25%) was added, the vial was lidded and put into the microwave reactor, then the reaction was carried out at 150° C. for 40 min. The reaction mixture was poured into 50 mL of saturated brine and extracted with ethyl acetate, the extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90° C.)=1/20, as an eluent) to give 0.25 g of compound 391 as yellow solid, m.p. 218-219° C.

¹H-NMR spectrum (300 MHz, internal standard: TMS, solvent CDCl₃) δ (ppm): 1.70 (s, 3H), 3.09 (d, 3H), 8.25 (d, 1H), 8.31 (s, 2H), 9.12 (s, 1H), 9.58 (s, 1H).

Other compounds of the present invention were prepared according to the above examples.

Physical properties and ¹HNMR spectrum (¹HNMR, 300 MHz, internal standard: TMS, ppm) of some compounds of this invention are as follows:

Compound 1: m.p. 136-138° C. δ (CDCl₃): 2.12 (s, 3H), 7.21 (m, 2H), 7.26 (m, 1H), 8.72 (s, 1H), 9.00 (s, 1H).

Compound 4: m.p. 142-143° C. δ (CDCl₃): 2.20 (s, 3H), 6.59 (s, 1H), 7.58 (s, 1H), 8.67 (s, 1H), 8.80 (s, 1H).

Compound 5: m.p. 160-162° C. δ (CDCl₃): 1.95 (s, 3H), 7.41 (s, 2H), 8.72 (s, 1H), 9.19 (s, 1H).

Compound 7: m.p. 184-186° C. δ (CDCl₃): 2.22 (s, 3H), 6.87 (d, 2H), 7.62 (d, 2H), 8.66 (s, 1H), 8.93 (s, 1H).

Compound 8: m.p. 172-174° C. δ (DMSO): 2.34 (s, 3H), 6.83 (d, 2H), 8.06 (d, 2H), 8.64 (s, 1H), 9.49 (s, 1H).

Compound 9: m.p. 185-186° C. δ (CDCl₃): 2.41 (s, 3H), 6.56 (d, 1H), 8.31 (d, 1H), 8.52 (s, 1H), 9.23 (s, 1H), 10.59 (s, 1H).

Compound 10: a red oil. δ (CDCl₃): 2.27 (s, 3H), 8.52 (s, 1H), 9.09 (s, 2H), 10.93 (s, 1H).

Compound 12: m.p. 91-94° C. δ (CDCl₃): 2.14 (s, 3H), 6.91 (d, 2H), 7.21 (d, 2H), 8.71 (s, 1H), 9.20 (s, 1H).

Compound 28: m.p. 158-160° C. δ (CDCl₃): 2.10 (s, 3H), 6.83 (d, 4H), 7.12 (m, 2H), 7.34 (m, 4H), 8.56 (s, 1H).

Compound 31: m.p. 106-108° C. δ (CDCl₃): 2.22 (s, 3H), 6.55 (d, 1H), 7.43 (d, 1H), 7.75 (s, 1H), 8.65 (s, 1H), 8.87 (s, 1H).

Compound 32: m.p. 191-193° C. δ (CDCl₃): 2.29 (s, 3H), 6.48 (d, 1H), 8.06 (d, 1H), 8.41 (s, 1H), 8.62 (s, 1H), 8.79 (s, 1H).

Compound 33: m.p. 206-208° C. δ (CDCl₃): 2.25 (s, 3H), 6.48 (d, 1H), 7.47 (d, 1H), 7.77 (s, 1H), 8.62 (s, 1H), 8.80 (s, 1H).

Compound 34: m.p. 121-123° C. δ (CDCl₃): 2.02 (s, 3H), 2.40 (s, 3H), 6.53 (d, 1H), 7.10 (d, 1H), 7.27 (s, 1H), 8.74 (s, 1H), 9.03 (s, 1H).

Compound 36: m.p. 204-205° C. δ (CDCl₃): 2.31 (s, 3H), 6.48 (d, 1H), 7.43 (d, 1H), 8.26 (s, 1H), 8.54 (s, 1H), 10.36 (s, 1H).

Compound 39: m.p. 148-150° C. δ (CDCl₃): 2.07 (s, 3H), 7.53 (s, 1H), 7.72 (s, 1H), 8.71 (s, 1H), 8.97 (s, 1H).

Compound 41: m.p. 154-156° C. δ (CDCl₃): 2.21 (s, 3H), 7.20 (m, 1H), 7.80 (m, 1H), 8.59 (s, 1H), 9.94 (s, 1H).

Compound 42: m.p. 140-142° C. δ (CDCl₃): 2.17 (s, 3H), 7.19 (d, 2H), 8.71 (s, 1H), 8.94 (s, 1H).

Compound 44: m.p. 143-144° C. δ (CDCl₃): 1.98 (s, 3H), 7.66 (s, 2H), 8.70 (s, 1H), 9.10 (s, 1H).

Compound 45: m.p. 180-182° C. δ (CDCl₃): 1.99 (s, 3H), 7.69 (s, 2H), 8.67 (s, 1H), 9.00 (s, 1H).

Compound 47: m.p. 241-243° C. δ (CDCl₃): 1.97 (s, 3H), 7.83 (s, 2H), 8.69 (s, 1H), 9.11 (s, 1H).

Compound 51: m.p. 259-261° C. δ (CDCl₃): 2.38 (s, 3H), 6.54 (d, 1H), 7.70 (d, 1H), 8.50 (s, 1H), 8.62 (s, 1H), 10.51 (s, 1H).

Compound 61: m.p. 160-162° C. δ (CDCl₃): 2.18 (s, 3H), 7.88 (d, 1H), 8.32 (d, 1H), 8.55 (s, 1H), 9.97 (s, 1H).

Compound 62: m.p. 169-171° C. δ (CDCl₃): 2.26 (s, 3H), 8.50 (d, 2H), 8.99 (s, 1H), 10.14 (s, 1H).

Compound 63: m.p. 204-206° C. δ (CDCl₃): 2.23 (s, 3H), 7.87 (s, 1H), 8.38 (s, 1H), 8.51 (s, 1H), 10.00 (s, 1H).

Compound 67: m.p. 187-190° C. δ (CDCl₃): 2.18 (s, 3H), 8.23 (s, 2H), 8.57 (s, 1H), 10.39 (s, 1H).

Compound 69: m.p. 93-95° C. δ (CDCl₃): 2.19 (s, 3H), 8.14 (s, 2H), 8.56 (s, 1H), 10.42 (s, 1H).

Compound 77: an orange oil. δ (DMSO): 2.33 (s, 3H), 6.92 (d, 1H), 7.26 (s, 1H), 7.78 (d, 1H), 8.63 (s, 1H), 9.54 (s, 1H).

Compound 78: m.p. 204-206° C. δ (DMSO): 2.32 (s, 3H), 7.03 (s, 1H), 8.73 (s, 1H), 8.86 (s, 1H), 10.40 (s, 1H).

Compound 79: m.p. 125-127° C. δ (CDCl₃): 1.94 (s, 3H), 7.53 (s, 2H), 8.75 (s, 1H), 9.29 (s, 1H).

Compound 81: m.p. 160-161° C. δ (CDCl₃): 2.13 (s, 3H), 2.54 (s, 3H), 6.40 (d, 1H), 7.19 (d, 1H), 8.68 (s, 1H), 8.96 (s, 1H).

Compound 83: m.p. 110-112° C. δ (CDCl₃): 2.03 (s, 3H), 2.50 (s, 3H), 6.50 (d, 1H), 7.05 (t, 1H), 7.24 (d, 1H), 8.73 (s, 1H), 9.06 (s, 1H).

Compound 84: m.p. 133-135° C. δ (CDCl₃): 2.03 (s, 3H), 2.50 (s, 3H), 6.53 (d, 1H), 7.06 (t, 1H), 7.21 (d, 1H), 8.74 (s, 1H), 9.08 (s, 1H).

Compound 86: m.p. 158-161° C. δ (CDCl₃): 2.16 (s, 3H), 2.61 (s, 3H), 6.47 (d, 1H), 7.67 (d, 1H), 8.69 (s, 1H), 8.85 (s, 1H).

Compound 88: m.p. 172-175° C. δ (DMSO): 2.32 (s, 3H), 8.49 (s, 1H), 8.68 (s, 2H), 9.50 (s, 1H).

Compound 90: m.p. 127-129° C. δ (CDCl₃): 2.36 (s, 3H), 6.55 (s, 1H), 8.40 (s, 1H), 8.54 (s, 1H), 10.31 (s, 1H).

Compound 91: m.p. 169-171° C. δ (CDCl₃): 2.32 (s, 3H), 6.42 (s, 1H), 8.20 (s, 11-1), 8.60 (s, 1H), 8.62 (s, 1H).

Compound 96: m.p. 159-162° C. δ (CDCl₃): 2.16 (s, 314), 8.23 (s, 1H), 8.63 (s, 1H), 8.91 (s, 1H).

Compound 97: m.p. 133-135° C. δ (CDCl₃): 2.07 (s, 3H), 7.70 (s, 1H), 8.69 (s, 1H), 9.22 (s, 1H).

Compound 101: m.p. 96-97° C. δ (CDCl₃): 2.21 (s, 3H), 5.08 (m, 1H), 6.59 (s, 1H), 7.49 (s, 1H), 8.66 (s, 1H), 8.78 (s, 1H).

Compound 102: m.p. 192-194° C. δ (CDCl₃): 2.20 (s, 3H), 7.05 (s, 2H), 8.04 (s, 1H), 8.22 (s, 1H), 9.07 (s, 1H), 9.43 (s, 1H).

Compound 106: m.p. 112-114° C. δ (CDCl₃): 2.18 (s, 3H), 6.38 (s, 1H), 7.38 (d, 1H), 7.50 (s, 1H), 7.97 (d, 1H), 8.11 (s, 1H).

Compound 109: m.p. 146-148° C. δ (CDCl₃): 2.19 (s, 3H), 6.70 (d, 2H), 7.36 (d, 1H), 7.53 (d, 21-1), 7.96 (d, 1H), 8.20 (s, 1H).

Compound 110: m.p. 136-138° C. δ (CDCl₃): 2.22 (s, 3H), 6.70 (d, 2H), 7.41 (d, 1H), 8.00 (d, 1H), 8.16 (d, 2H), 8.22 (s, 1H).

Compound 113: m.p. 72-74° C. δ (CDCl₃): 2.12 (s, 3H), 6.75 (d, 2H), 7.12 (d, 2H), 7.25 (d, 1H), 7.98 (d, 1H), 8.46 (s, 1H).

Compound 116: a red oil. δ (CDCl₃): 2.02 (s, 3H), 2.38 (s, 3H), 6.34 (d, 1H), 7.00 (d, 114), 7.18 (m, 2H), 7.98 (d, 1H), 8.30 (s, 1H).

Compound 120: a brown oil. δ (CDCl₃): 1.92 (s, 3H), 7.22 (d, 114), 7.58 (s, 2H), 7.93 (d, 1H), 8.39 (s, 1H).

Compound 126: m.p. 158-160° C. δ (CDCl₃): 2.30 (s, 3H), 6.47 (d, 1H), 7.59 (m, 2H), 7.94 (d, 1H), 8.60 (s, 1H), 10.21 (s, 1H).

Compound 136: m.p. 136-138° C. δ (CDCl₃): 2.22 (s, 3H), 6.75 (d, 1H), 7.03 (s, 1H), 7.45 (d, 1H), 7.67 (d, 1H), 7.99 (d, 1H), 8.16 (s, 1H).

Compound 347: m.p. 134-136° C. δ (CDCl₃): 1.79 (s, 3H), 3.96 (s, 3H), 8.29 (s, 2H), 8.74 (s, 1H), 9.18 (s, 1H).

Compound 369: m.p. 132-134° C. δ (CDCl₃): 2.11 (s, 3H), 2.39 (s, 3H), 8.29 (s, 214), 8.47 (s, 1H), 8.95 (s, 1H).

Compound 413: m.p. 178-180° C. δ (CDCl₃): 1.71 (s, 3H), 2.86 (s, 6H), 8.29 (s, 2H), 8.66 (s, 1H), 9.45 (s, 1H).

Compound 457: m.p. 126-128° C. δ (CDCl₃): 1.83 (s, 3H), 4.42 (q, 2H), 8.30 (s, 2H), 8.85 (s, 1H), 9.20 (s, 1H).

Compound 501: m.p. 151-153° C. δ (CDCl₃): 1.99 (s, 3H), 8.31 (d, 1H), 8.47 (d, 1H), 8.66 (s, 1H), 9.00 (s, 1H).

Compound 502: m.p. 151-154° C. δ (CDCl₃): 1.97 (s, 3H), 8.49 (s, 2H), 8.68 (s, 1H), 9.03 (s, 1H).

Compound 503: m.p. 132-134° C. δ (CDCl₃): 1.95 (s, 3H), 3.96 (s, 3H), 8.05 (s, 2H), 8.70 (s, 1H), 9.13 (s, 1H).

Compound 504: m.p. 135-137° C. δ (CDCl₃): 2.16 (s, 3H), 7.95 (dd, 1H), 8.26 (t, 1H), 8.63 (s, 1H), 8.82 (s, 1H).

Compound 505: m.p. 131-132° C. δ (CDCl₃): 2.10 (s, 3H), 6.99 (t, 2H), 7.17 (m, 1H), 8.72 (s, 1H), 8.98 (s, 1H).

Compound 506: m.p. 148-150° C. δ (CDCl₃): 2.12 (s, 3H), 7.04 (d, 2H), 8.70 (s, 1H), 8.87 (s, 1H).

Compound 507: m.p. 140-142° C. δ (CDCl₃): 2.58 (s, 3H), 3.30 (s, 3H), 8.38 (s, 1H), 8.57 (s, 2H).

Compound 508: δ(CDCl₃): 1.94 (s, 3H), 3.03 (d, 3H), 7.78 (s, 2H), 8.70 (s, 1H), 9.14 (s, 1H).

Compound 509: m.p. 216-218° C. δ (CDCl₃): 1.56 (s, 3H), 3.04 (m, 6H), 7.80 (s, 2H), 8.18 (s, 1H), 9.13 (s, 1H), 9.58 (s, 1H).

Compound 510: m.p. 138-140° C. δ (CDCl₃): 2.58 (s, 3H), 3.37 (s, 3H), 7.23 (d, 1H), 7.48 (s, 1H), 7.57 (d, 1H), 8.08 (s, 1H).

Compound 511: m.p. 216-219° C. δ (CDCl₃): 2.30 (s, 3H), 7.88 (s, 2H), 8.48 (s, 1H), 8.85 (s, 1H).

Compound 521: m.p. 146-148° C. δ (CDCl₃): 1.86 (s, 3H), 2.40 (s, 3H), 7.18 (m, 2H), 7.28 (m, 1H), 8.80 (s, 1H), 9.52 (s, 1H).

Compound 522: m.p. 137-139° C. δ (CDCl₃): 1.91 (s, 3H), 2.31 (s, 3H), 8.10 (s, 1H), 8.21 (s, 1H), 8.73 (s, 1H), 9.20 (s, 1H).

FORMULATION EXAMPLES

The active ingredient can be selected from any compound of general formula I of the present invention, base on 100% active ingredient (Weight/Weight %).

Example 7 30% Wettable Powders

Compound 43 30% Sodium dodecyl sulfate  2% Lignin sulfonate  3% Naphthalene sulfonic acid  5% formaldehyde condensate Precipitated calcium carbonate Make up to 100%

The compound and other components are fully mixed, after smashing through ultrafine pulverizer, 30% wettable powder products were obtained.

Example 8 40% Suspension Concentrate

Compound 38  40% Glycol  10% Nonylphenols polyethylene glycol ether   6% Lignin sulfonate  10% Carboxymethyl cellulose   1% 37% of formaldehyde aqueous solution 0.2% 75% of silicone oil water emulsion 0.8% Water Make up to 100%

Fully mixing the compound and other components, suspension concentrate can be obtained, and then any required dilution can be obtained by diluting the above suspension concentrate with water.

Example 9 60% Water Dispersible Granules

Compound 38 60% Naphthalene sulfonate formaldehyde 12% condensate N-methyl-N-oil acyl - bovine sodium  8% Polyvinylpyrrolidone  2% Carboxymethyl cellulose  2% Kaolin Make up to 100%

The compound and other components were mixed and smashed, then kneaded together with water, added to the granulation 10-100 mesh machine for granulation, finally dried and sieved (at the scope screen).

Biological Testing

The compounds of the present invention showed excellent activity against a variety of plant pathogens/diseases in agricultural field, but didn't exhibit any herbicidal activity so far. The tests of compounds of the present invention against many kinds of plant diseases caused by fungi were carried out in vitro or in vivo. The results of fungicidal activity are listed in the following examples.

Example 10 Determination of the Activity In Vitro

The method is as follow:

High Through Put is used in the test. The compound is dissolved in a proper solvent to become a testing solution whose concentration is designed. The solvent is selected from acetone, methanol, DMF and so on according to their dissolving capability to the sample. In a no animalcule condition, the testing solution and pathogens suspension are added into the cells of 96 cells culture board, which then should be placed in the constant temperature box. 24 hours later, pathogen germination or growth can be investigated by eyeballing, and the activity in vitro of the compound is evaluated based on germination or growth of control treatment.

The activities in vitro (inhibition rate) of parts of the compounds are as follows:

The inhibition rate against rice blast (Magnaporthe grisea):

At the dose of 25 mg/L, the inhibition rate of compounds 2, 4, 5, 7, 8, 9, 10, 12, 28, 32, 36, 38, 39, 41, 42, 43, 44, 45, 47, 51, 62, 63, 67, 69, 77, 78, 79, 83, 84, 86, 88, 89, 90, 91, 96, 97, 102, 109, 110, 116, 126, 136, 347, 369, 413, 457, 501, 502, 503, 504, 506, 507 and so on was 100%;

At the dose of 2.8 mg/L, the inhibition rate of compounds 5, 9, 12, 32, 38, 39, 41, 42, 43, 44, 45, 51, 62, 63, 67, 69, 77, 78, 86, 89, 90, 91, 96, 97, 126, 347, 369, 413, 457, 501, 502, 503, 504, 506 was 100%, and that of compounds 2, 4, 8, 36, 79, 88 was 80%;

At the dose of 0.3 mg/L, the inhibition rate of compounds 38, 39, 42, 43, 44, 45, 67, 91, 97, 347, 369, 457, 501, 502, 504 was 100%, and that of compound 413 was 80%;

At the dose of 0.03 mg/L, the inhibition rate of compounds 42, 369, 504 was 100%, and that of compounds 43, 45, 347, 501 was 80%.

The inhibition rate against cucumber gray mold (Botrytis cinerea):

At the dose of 25 mg/L, the inhibition rate of compounds 38, 39, 42, 43, 44, 45, 62, 63, 67, 69, 78, 88, 89, 90, 91, 96, 97, 457 was 100%;

At the dose of 2.8 mg/L, the inhibition rate of compounds 38, 39, 42, 43, 44, 45, 62, 63, 67, 69, 78, 89, 91, 97, 457 was 100%, and that of compounds 88, 96 was 80%;

At the dose of 0.3 mg/L, the inhibition rate of compounds 42, 43, 45, 457 was 100%, and that of compounds 38, 39, 67, 97 was 80%;

At the dose of 0.03 mg/L, the inhibition rate of compound 42 was 100%.

Example 11 The Determination of Protectant Activity In Vivo

The method is as follow:

The whole plant is used in this test. The compound is dissolved in a proper solvent to get mother solution. The proper solvent is selected from acetone, methanol, DMF and so on according to their dissolving capability to the sample. The rate of solvent and testing solution (v/v) is equal to or less than 5%. The mother solution is diluted with water containing 0.1% tween-80 to get the testing solution whose concentration is designed. The testing solution is sprayed to the host plant by a special plant sprayer. The plant is inoculated with fungus after 24 hours. According to the infecting characteristic of fungus, the plant is stored in a humidity chamber and then transferred into greenhouse after infection is finished. And the other plants are placed in greenhouse directly. The activity of compound is obtained by eyeballing after 7 days in common.

The protectant activities in vivo of parts of the compounds are as follows:

The protectant activity against cucumber downy mildew (Pseudoperonospora cubensis) in vivo:

At the dose of 400 mg/L, the protectant activity of compounds 5, 9, 10, 32, 38, 39, 43, 44, 45, 62, 63, 67, 69, 77, 78, 88, 89, 91, 96, 413, 501, 522 was 100%, and that of compounds 41, 86, 391, 502, 503, 504, 507 was more than 90%;

At the dose of 100 mg/L, the protectant activity of compounds 5, 9, 10, 32, 38, 39, 43, 44, 45, 62, 63, 67, 69, 78, 88, 89 was 100%, that of compounds 77, 91, 96 was more than 95% and that of compounds 41, 86, 504 was no less than 85%;

At the dose of 50 mg/L, the protectant activity of compounds 9, 38, 39, 43, 44, 63, 67, 69, 78, 88 was 100%, that of compound 62 was 98% and that of compounds 32, 45, 91 was no less than 70%;

At the dose of 12.5 mg/L, the protectant activity of compounds 43, 63, 78 was 100%, and that of compounds 38, 44, 67, 91 was no less than 80%.

The protectant activity against corn rust (Puccinia sorghi) in vivo:

At the dose of 400 mg/L, the protectant activity of compounds 2, 12, 32, 34, 38, 41, 42, 43, 44, 63, 67, 78, 84, 89, 102, 347, 502 was 100%, that of compounds 36, 88, 136, 369, 413, 501, 503, 504, 505 was no less than 95% and that of compounds 4, 39, 69, 81, 110, 116, 120, 391 was no less than 80%;

At the dose of 100 mg/L, the protectant activity of compounds 43, 44, 78, 347, 369, 502 was 100%, and that of compounds 34, 67, 84, 88, 413, 501was no less than 80%;

At the dose of 25 mg/L, the protectant activity of compounds 347, 369 was 100%, and that of compounds 34, 44, 88, 502 was no less than 60%;

At the dose of 6.25 mg/L, the protectant activity of compound 347 was 100%, and that of compound 369 was 85%.

The protectant activity against wheat powdery mildew (Blumeria graminis) in vivo:

At the dose of 400 mg/L, the protectant activity of compound 63 was 100%, and that of compounds 43, 45, 67, 90 was no less than 80%.

The protectant activity against cucumber anthracnose (Colletotrichum lagenarium) in vivo:

At the dose of 400 mg/L, the protectant activity of compounds 43, 44, 78 was 100%.

Example 12 The Test Results of Parts of Compounds and Contrasts

Contrastive tests were carried out between parts of compounds, contrasts and intermediates. The test results are listed in table 7-table 11 (“/” in the following tables means no test).

TABLE 7 The protectant activity against cucumber downy mildew in vivo Protectant activity (%) 50 12.5 3.125 Compd. No. mg/L mg/L mg/L 38 100 80 65 43 100 100 90 44 100 85 45 45 80 65 55 67 100 80 40 69 100 70 40 78 100 100 60 91 95 80 75 intermediate B 0 0 0 intermediate C 0 0 0 diphenylamine 0 0 0 fluazinam 100 95 40 dimethomorph 100 80 35 contrast ACS 0 0 0

Contrast ACS was reported in ACS Symposium Series (1992), 504 (Synth. Chem. Agrochem. III), 341-48, its structure is as follow:

TABLE 8 The protectant activity against corn rust in vivo: Protectant activity (%) 100 25 6.25 Compd. No. mg/L mg/L mg/L 34 80 75 20 38 70 20 0 44 75 60 15 84 90 30 0 88 90 60 0 347 100 100 100 369 100 100 85 413 85 30 0 501 85 50 30 502 100 60 20 fluazinam 90 30 10 contrast ACS 0 0 0

TABLE 9 The activity against rice blast and cucumber gray mold in vitro Inhibition rate against Inhibition rate against rice blast (%) cucumber gray mold (%) Compd. No. 0.3 mg/L 0.03 mg/L 0.3 mg/L 0.1 mg/L 0.03 mg/L 38 / / 80 50 0 39 / / 80 50 0 42 100 100 100 100 100 43 100 80 100 100 50 45 100 80 100 100 0 347 100 80 / / / 369 100 100 / / / 457 100 50 100 80 0 501 100 80 / / / 502 100 50 / / / 504 100 100 / / / fluazinam 100 50 100 80 0 contrast ACS 0 0 0 0 0

TABLE 10 Contrastive results of compound 43 and contrast ACS Protectant activity against cucumber downy Activity against rice mildew in vivo (%) blast in vitro (%) Compd. 100 50 25 25 8.3 2.8 0.9 No. mg/L mg/L mg/L mg/L mg/L mg/L mg/L 5 100 40 30 100 100 100 100 contrast / 0 0 0 0 0 0 ACS

TABLE 11 Contrastive results of compound 43 and fluazinam Activity in vitro (%) Target fungus Compound 10 mg/L 1 mg/L 0.1 mg/L rice sheath blight compound 43 100 95 74 (Rhizoctonia solani Palo) fluazinam 97 83 69 corn southern leaf blight compound 43 100 100 54 (Helminthosporium maydis) fluazinam 100 92 41 cucumber fusarium wilt compound 43 99 91 79 (Fusarium oxysporum f. sp.) fluazinam 92 85 56 pear scab (Fusicladium compound 43 100 99 87 pirina) fluazinam 94 89 47 cotton nthracnose compound 43 100 100 94 (Colletotrichum gossypii Southw.) fluazinam 100 97 71 cotton verticillium wilt compound 43 100 100 82 (Verticillium dahliae Kleb) fluazinam 100 96 46 rape sclertiniose compound 43 100 100 88 (Sclerotinia sclerotiorum) fluazinam 100 97 57 

We claim:
 1. A substituted diphenylamine compound having general formula I:

wherein: R₁ is selected from H, C₁-C₁₂alkyl, C₃-C₁₂cycloalkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂haloalkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkoxyC₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylaminothio, C₂-C₁₂ dialkylaminothio or CO—X—CO₂R₉, in which X is selected from (CHR₉)n, CR₉═CR₁₀ or C₆H₄, n=1-6; R₂ is selected from halogen, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₁-C₁₂alkylsulfonyl, C₃-C₁₂cycloalkyl, C₂-C₁₂dialkylamino, C₃-C₁₂alkenyloxy, C₃-C₁₂haloalkenyloxy, C₃-C₁₂alkynyloxy, C₃-C₁₂haloalkynyloxy, C₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkylcarbonylamino, C₁-C₁₂alkylsulfonyloxy, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkoxy, or the following groups unsubstituted or substituted with 1-5 R₁₁: aryloxy, arylamino, arylmethoxy, arylmethylamino, heteroaryloxy or heteroarylamino, and when the number of the substitutes is more than 1, R₁₁ may be the same or different; R₃ is selected from H, halogen, NO₂, CN, C(═O)NR₉R₁₀, C(═S)NR₉R₁₀, C₁-C₁₂alkylaminocarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂haloalkyl or C₁-C₁₂alkylsulfonyl; R₄ and R₈ may be the same or different, respectively selected from H, halogen, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, or the following groups unsubstituted or substituted with 1-5 R₁₁: aryl, arylmethyl, aryloxy, arylamino, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, arylaminocarbonyl or heteroaryloxy, and when the number of the substitutes is more than 1, R₁₁ may be the same or different; R₅ and R₇ may be the same or different, respectively selected from H, halogen, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₁-C₁₂alkylamino, C₁-C₁₂haloalkylamino, C₁-C₁₂alkylthio, C₁-C₁₂haloalkylthio, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkylcarbonyloxy, C₁-C₁₂alkoxycarbonyloxy, C₁-C₁₂alkylaminocarbonyloxy, C₁-C₁₂alkylsulfonyloxy, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂haloalkoxyC₁-C₁₂haloalkoxy, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkoxy, or the following groups unsubstituted or substituted with 1-5 R₁₁: aryl, arylmethyl, aryloxy, arylamino, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, arylaminocarbonyl or heteroaryloxy, and when the number of the substitutes is more than 1, R₁₁ may be the same or different; R₆ is selected from H, halogen, CN, NO₂, CO₂H, C(═O)NR₉R₁₀, C₁-C₁₂alkyl, C₁-C₁₂haloalkyl, C₁-C₁₂alkoxy, C₁-C₁₂haloalkoxy, C₂-C₁₂alkenyl, C₂-C₁₂alkynyl, C₁-C₁₂alkylsulfonyl, C₁-C₁₂alkylcarbonyl, C₁-C₁₂alkoxycarbonyl, C₁-C₁₂alkoxyC₁-C₁₂alkyl, C₁-C₁₂alkoxycarbonylC₁-C₁₂alkyl, C₁-C₁₂alkoxyC₁-C₁₂alkoxy, C₁-C₁₂haloalkoxyC₁-C₁₂haloalkoxy, or the following groups unsubstituted or substituted with 1-5 R₁₁: aryl, arylmethyl, aryloxy, arylamino, arylcarbonyl, arylmethylcarbonyl, aryloxycarbonyl, arylaminocarbonyl or heteroaryloxy, and when the number of the substitutes is more than 1, R₁₁ may be the same or different; but R₄, R₅, R₆, R₇ and R₈ can not be H simultaneously; R₉ and R₁₀ may be the same or different, respectively selected from H or C₁-C₆alkyl; R₁₁ is selected from halogen, NO₂, ON, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylthio, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆alkynyloxy, C₃-C₆haloalkynyloxy, C₁-C₆haloalkylthio, C₁-C₆haloalkylcarbonyl, C₁-C₆alkylamino, C₁-C₆haloalkylamino, C₂-C₈dialkylamino, C₁-C₆alkylcarbonylamino, C₁-C₆haloalkylcarbonylamino, C₁-C₆alkylaminocarbonyl or C₁-C₆haloalkylaminocarbonyl; or the salts of the compounds having general formula I.
 2. The compound according to the claim 1, characterized in that wherein general formula I: R₁ is selected from H, C₁-C₆alkyl, C₃-C₆cycloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆haloalkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfonyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkoxyC₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, C₁-C₆alkylaminothio, C₂-C₆ dialkylaminothio or CO—X—CO₂R₉, in which X is selected from (CHR₉)n, CR₉═CR₁₀ or C₆H₄, n=1-3; R₂ is selected from halogen, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylamino, C₁-C₆haloalkylamino, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₁-C₆alkylsulfonyl, C₂-C₆dialkylamino, C₃-C₆alkenyloxy, C₃-C₆haloalkenyloxy, C₃-C₆alkynyloxy, C₁-C₆alkylcarbonyloxy, C₁-C₆alkylcarbonylamino, C₁-C₆alkylsulfonyloxy, C₁-C₆alkoxyC₁-C₆alkoxy, C₁-C₆alkoxycarbonylC₁-C₆alkoxy, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, benzyloxy, benzylamino, pyridyloxy or pyridylamino; R₃ is selected from Cl, Br, F, NO₂, CN, C(═O)NR₉R₁₀, C(═S)NR₉R₁₀, CO₂CH₃, CF₃ or SO₂CH₃; R₄ and R₈ may be the same or different, respectively selected from H, halogen, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, or the following groups unsubstituted or substituted with 1-4 R₁₁: phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy; R₅ and R₇ may be the same or different, respectively selected from H, halogen, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₁-C₆alkylamino, C₁-C₆haloalkylamino, C₁-C₆alkylthio, C₁-C₆haloalkylthio, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkoxyC₁-C₆alkyl; R₆ is selected from H, halogen, CN, NO₂, CO₂H, C(═O)NR₉R₁₀, C₁-C₆alkyl, C₁-C₆haloalkyl, C₁-C₆haloalkoxy, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkylsulfonyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkoxycarbonylC₁-C₆alkyl, C₁-C₆alkoxyC₁-C₆alkoxy, or the following groups unsubstituted or substituted with 1-4 R₁₁: phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy; but R₄, R₅, R₆, R₇ and R₈ can not be H simultaneously; R₉ and R₁₀ may be the same or different, respectively selected from H or C₁-C₃alkyl; R₁₁ is selected from halogen, NO₂, CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkylamino, C₂-C₆dialkylamino, C₁-C₃alkylcarbonylamino or C₁-C₃alkylaminocarbonyl; or the salts of the compounds having general formula I.
 3. The compound according to the claim 2, characterized in that wherein general formula I: R₁ is selected from H, C₁-C₃alkyl, C₃-C₆cycloalkyl, C₁-C₃alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃haloalkylthio, C₁-C₃alkylsulfonyl, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃alkoxyC₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, C₁-C₃alkylaminothio, C₂-C₆ dialkylaminothio or CO—X—CO₂R₉, in which X is selected from (CHR₉)n, CR₉═CR₁₀ or C₆H₄, n=1-3; R₂ is selected from Cl, Br, F, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, C₁-C₃alkylthio, C₁-C₃haloalkylthio, C₁-C₃alkylsulfonyl, C₂-C₆dialkylamino, C₃-C₄alkenyloxy, C₃-C₄haloalkenyloxy, C₃-C₄alkynyloxy, C₁-C₃alkylcarbonyloxy, C₁-C₃alkylcarbonylamino, C₁-C₃alkylsulfonyloxy, C₁-C₃alkoxyC₁-C₃alkoxy, C₁-C₃alkoxycarbonylC₁-C₃alkoxy, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, benzyloxy, benzylamino, pyridyloxy or pyridylamino; R₃ is NO₂, R₄ and R₈ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₂-C₃alkenyl, C₂-C₃alkynyl, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy; R₅ and R₇ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, C₁-C₃alkylthio, C₁-C₃haloalkylthio, C₂-C₃alkenyl, C₂-C₃alkynyl, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl or C₁-C₃alkoxyC₁-C₃alkyl; R₆ is selected from H, Cl, Br, F, CN, NO₂, CO₂H, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃haloalkoxy, C₂-C₃alkenyl, C₂-C₃alkynyl, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxyC₁-C₆alkyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, C₁-C₃alkoxyC₁-C₃alkoxy, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl, anilinocarbonyl or pyridyloxy; but R₄, R₅, R₆, R₇ and R₈ can not be H simultaneously; R₉ and R₁₀ may be the same or different, respectively selected from H or C₁-C₃alkyl; R₁₁ is selected from Cl, Br, F, NO₂, CN, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, or C₁-C₃alkylaminocarbonyl; or the salts formed from the compounds of general formula I with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methylsulfonic acid, p-toluenesulfonic acid, malic acid or citric acid.
 4. The compound according to the claim 3, characterized in that wherein general formula I: R₁ is selected from H, C₁-C₃alkyl, C₃-C₆cycloalkyl, C₁-C₃alkylcarbonyl, C₁-C₃haloalkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃haloalkylthio, C₁-C₃alkylsulfonyl, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃alkoxyC₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, C₁-C₃alkylaminothio, C₂-C₆ dialkylaminothio, COCH₂CO₂R₉

COCH₂CH₂CO₂R₉

COCHCH₃CO₂R₉

COC₆H₄CO₂R₉ or COCH═CHCO₂R₉; R₂ is selected from Cl, Br, F, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, C₁-C₃alkylthio, C₁-C₃haloalkylthio, C₁-C₃alkylsulfonyl, C₂-C₆dialkylamino, C₃-C₄alkenyloxy, C₃-C₄haloalkenyloxy, C₃-C₄alkynyloxy, C₁-C₃alkoxyC₁-C₃alkoxy, C₁-C₃alkoxycarbonylC₁-C₃alkoxy, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, benzyloxy, benzylamino, pyridyloxy or pyridylamino; R₃ is NO₂, R₄ and R₈ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxyC₁-C₃alkyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, anilino, phenoxycarbonyl or anilinocarbonyl; R₅ and R₇ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, C₁-C₃alkylthio, C₁-C₃haloalkylthio, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl or C₁-C₃alkoxyC₁-C₃alkyl; R₆ is selected from H, Cl, Br, F, CN, NO₂, CO₂H, C(═O)NR₉R₁₀, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃haloalkoxy, C₂-C₃alkenyl, C₂-C₃alkynyl, C₁-C₃alkylsulfonyl, C₁-C₃alkylcarbonyl, C₁-C₃alkoxycarbonyl, C₁-C₃alkoxyC₁-C₆alkyl, C₁-C₃alkoxycarbonylC₁-C₃alkyl, C₁-C₃alkoxyC₁-C₃alkoxy, or the following groups unsubstituted or substituted with 1-3 R₁₁: phenoxy, phenylcarbonyl, benzylcarbonyl, phenoxycarbonyl or anilinocarbonyl; but R₄, R₅, R₆, R₇ and R₈ can not be H simultaneously; R₉ and R₁₀ may be the same or different, respectively selected from H, CH₃ or C₂H₅; R₁₁ is selected from Cl, Br, F, NO₂, CN, CF₃, CH₃, OCH₃, SCH₃, formyl, CO₂CH₃ or CONHCH₃; or the salts formed from the compounds of general formula I with hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, methylsulfonic acid, p-toluenesulfonic acid, malic acid or citric acid.
 5. The compound according to the claim 4, characterized in that wherein general formula I: R₁ is selected from H, CH₃, C₂H₅, cyclopropyl, formyl, COCH₃, COCF₃, CO₂CH₃, CO₂C₂H₅, SCCl₃, SO₂CH₃, SO₂C₂H₅, CH₂OCH₃, CH₂OO₂H₅, CH₂CH₂OCH₃, COCH₂OCH₃, CH₂COOCH₃, SNHCH₃, SN(CH₃)₂, COCH₂CO₂H, COCH₂CO₂CH₃, COCH₂CH₂CO₂H, COCH₂CH₂CO₂CH₃, COCHCH₃CO₂H, COCHCH₃CO₂CH₃, COC₆H₄CO₂H, COC₆H₄CO₂CH₃, COCH═CHCO₂H or COCH═CHCO₂CH₃; R₂ is selected from Cl, Br, F, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylamino, C₁-C₃haloalkylamino, SCH₃, SC₂H₅, N(CH₃)₂, N(C₂H₅)₂, OCH₂OCH₃, OPh, NHPh, OCH₂Ph, NHCH₂Ph, 4-chlorophenoxy, 4-chlorophenylamino, 2-chloro-4-(trifluoromethyl)phenoxy, 2-chloro-4-(trifluoromethyl)phenylamino, 3-chloro-5-(trifluoromethyl)pyridin-2-yloxy or 3-chloro-5-(trifluoromethyl)pyridin-2-ylamino; R₃ is NO₂, R₄ and R₈ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NH₂, C(═O)NHCH₃, C(═O)N(CH₃)₂, CH₃, C₂H₅, CF₃, OCH₃, OC₂H₅, OCF₃, SO₂CH₃, SO₂C₂H₅, COCH₃, COC₂H₅, CO₂CH₃, CO₂C₂H₅, OPh, NHPh, CO₂Ph or CONHPh; R₅ and R₇ may be the same or different, respectively selected from H, Cl, Br, F, CN, NO₂, C(═O)NH₂, CH₃, CF₃, OCH₃, OCF₃, NHCH₃, SCH₃, SO₂CH₃, SO₂C₂H₅, COCH₃, COC₂H₅, CO₂CH₃, CO₂C₂H₅ or CH₂OCH₃; R₆ is selected from H, Cl, Br, F, CN, NO₂, CO₂H, C(═O)NH₂, C(═O)NHCH₃, C(═O)N(CH₃)₂, CH₃, CF₃,

CF(CF₃)₂

OCF₃

OCH₂CF₃

OCF₂CHFCF₃

SO₂CH₃, SO₂C₂H₅

COCH₃, COC₂H₅, CO₂CH₃, CO₂C₂H₅

OPh, NHPh,

COPh

COCH₂Ph

CO₂Ph

CONHPh

pyridinoxy or 3-chloro-5-(trifluoromethyl)pyridin-2-yloxy; but R₄, R₅, R₆, R₇ and R₈ can not be H simultaneously; or the salts formed from the compounds of general formula I with hydrochloric acid, sulfuric acid, phosphoric acid, trifluoroacetic acid, methylsulfonic acid or p-toluenesulfonic acid.
 6. A fungicidal composition comprising the compound according to claim 1 as an active ingredient and an acceptable carrier in agriculture, wherein the weight percentage of the active ingredient in the composition is 0.5-90%. 